


Buy Me A Drink First

by PaperAnn



Category: Supernatural
Genre: Alternate Universe - Modern Setting, Anal Sex, Bachelorette Party, Bottom Dean, Drunken Shenanigans, Fluff and Humor, M/M, Multi, Oral Sex, POV Dean Winchester, Phone Sex, Rimming, Romantic Comedy, Sequel Included, Shower Sex, Smut, Top Castiel, Weddings
Language: English
Status: Completed
Published: 2014-12-18
Updated: 2015-02-01
Packaged: 2018-03-02 00:24:46
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 10
Words: 56,565
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/2793080
Author URL: https://archiveofourown.org/users/PaperAnn/pseuds/PaperAnn
Summary: <blockquote class="userstuff">
              <p>Buy Me A Drink First<br/>Chapters 1-2<br/>Dean wasn’t sure how he got roped into being Jo’s “bodyguard” for her bachelorette party.  Maybe it had something to do with being promised a wild night of drinking?  And he could do wild nights of drinking.  But he hadn't taken into account that bars in Chicago didn't close until 4 or 5am, and Chicago was their destination.  He also didn't take into account shots of ‘Kinky’ at 7pm, monitoring nearly a dozen bridesmaids, and accidentally starting cat fights at a gay bar. Oh, and then there was a tall, dark and mouthy Russian named Castiel, or something, at the end of the night.  Awesome.</p><p>Dean Winchester +1<br/>Chapters 3-10<br/>So Dean considered himself a man of good ideas. Great ideas, for the most part. On the other hand, he had just as many terrible ones. He hadn’t decided which of those two options <i>this</i> was. The entire situation was unorthodox. Obviously. How the hell did he end up asking a one night stand to be his +1 to his best friend’s wedding? And why the hell did said one night stand agree?</p>
            </blockquote>





	1. Chapter 1

**Author's Note:**

> This fic goes out to all my wonderful readers who never fail to inspire me with so much amazing feedback. Huge shout out to those who've journeyed back through my archive to comment on old works, it warms my heart <3 You're fantastic and I love you so much!

The first thing Dean Winchester did when he walked into the hotel was whistle, long and appreciatively. His best friend, Jo, had _really_ gone all out with this one. They were located on the thirteenth floor of a snazzy hotel, in the presidential suite or something where the sheets on the bed might has well have been stitched with gold. There was a connecting room, with just as much glamour as the one he was currently drooling over, only a slightly different layout.

“Stop gaping, Winchester,” Jo teased, as she punched him in the shoulder and set her rolling suitcase alongside one of the beds. “It’s my last night of freedom with the girls, I could afford to splurge a little!”

“A little?!” Dean demanded, as he dove onto one of the mattresses and rolled. “Dude, this is like _Versailles_.”

“Just because some of us prefer the nicer things in life, as opposed to a scummy motel room, doesn’t mean you have to knock it!” The blonde launched herself to tackle the man she considered to be her big brother. “Enjoy, peasant!”

“Shut your face! You know you love those ‘scummy motel rooms,’ just as much as me!”

“Do not!"

“Rags to riches, bitch!” Charlie announced, as she caught the tail end of their conversation, waltzing into the room. She pulled the trendy sunglasses off her face, and raised an eyebrow, “Should I give you two some privacy? Is this your ‘last fling before the ring,’ Miss Harvelle?”

“Eww! Gross, Charlie!” Jo smashed Dean’s face with her palm, “That’s, like, incest!”

“Don’t knock it, til you’ve tried it,” Dean winked, as soon as his face was visible again.

“I’m telling Sam you said that!”

“Oh, god. Am I gonna have to take this abuse all night?” Dean groaned, “I should’ve never agreed to this 'bodyguard' bullshit.”

“But we neeeed youuu!” Charlie gracefully fell on the bed to the other side of Dean, “Obvis. Can’t let all these hot girls loose in the city without someone with big muscles protecting them, right?”

“You’re all _animals_ , I’m sure you’ll do just fine!” His retort had no real venom behind it, if anything, he spoke fondly. “I expect free drinks, as payment.”

“Hah! You can flirt your way into free drinks all by yourself, slut,” with a shimmy of her shoulders, Jo stood up.

She pulled out her cellphone, to glance at the time and looked thoughtful for a second. “I know some of the girls went to dinner to wait for us to check in, but they should be here soon. We can start getting ready, Char. I think Anna and Tess will be here pretty quick, they were right behind us on the expressway. Until _someone_ decided it would be fun to run a few yellow lights and lose them.”

“Hey! Baby’s got a mind of her own, and doesn’t wanna be stuck in this fuckin’ city traffic any longer than she has to be!”

“Was it _Baby_ who also nearly chewed the hotel valet’s arm off when he asked for the keys to park her?”

“Yep. She was crying on the inside.”

“You’re such a drama queen, and that’s coming from _me_.” Charlie stabbed him in the chest a few times with a pointed finger, “You know they get paid to do that, right? And if by any terrible natural disaster or supernatural tragedy she gets a nick or a scrape they’ll cover the damages?”

“With their lives.” Dean deadpanned, his face serious and his glare icy.

“Drama. Queen.”

There was a loud knock on the door, before Jo threw it open and greeted Anna and Tessa with open arms. She muttered apologizes about Dean’s ‘asshole driving,’ and gave them a brief tour of the rooms. The girls were much less awestruck than he had been, which made him feel like even _more_ of a peasant. _Sorry_ , he didn’t grow up in rich families and hadn’t had a chance to become desensitized by life’s ‘finery.’ He wasn’t bitter. Really, he wasn’t. How Jo made all these ritzy friend, he never knew. At least they were hot, ritzy friends.

“The other girls will be here soon! Dean, you wanna go grab some ice and I’ll get the shot glasses ready for when the cavalry arrives?” There was a devilish smirk on her face as she handed him the ice bucket.

“Yes, yes, your majesty!” And with an exaggerated bow, he left the room.

Dean tucked the tub under his arm and looked at the signs on the walls. There were arrows directing to the pool, laundry room, gym... _Really_? Who wanted to go to the _gym_ when they were on a vacation or business trip? And finally, there were signs pointing to the vending machines and the ice machine.

He strolled back to where he’d come from, the hallways seeming _endless_ until he finally reached his destination. Right before he turned the corner, he heard the musical ‘ding’ of the elevator, and out from it poured a giggling group of women. They were all in different types of heels, dressed to the nines, hair perfectly curled, or pinned up and strutting down the hall. Dean didn’t even hesitate to check out the few asses that weren’t obstructed by jackets.

And those were some _fine asses_.

A goofy grin melted his frown until he realized _where_ they were ‘stomping it out’ to. Right to where he’d come from. Right to the suite. _Shit_. These were the rest of Jo’s bridesmaids?!

How the fuck many did she have?!

\-------------------

There was whooping and laughing when Dean walked back in the room with the promised ice, and shot glasses filled with a syrupy pink liquid were being handed out when Jo quickly snagged the bucket and jammed the fifth in it. He rolled his eyes when a drink was shoved in his hand and muttered, “Room temperature, round one, eh?”

“It’s a _celebration_ , now that everyone’s here!” She gave him a _look_ that dared him to give her any sass back.

Which Dean did not do. It was the _look_ that both her and her mother mastered - one that was nearly a promise of death, if disobeyed. So instead, he gulped and nodded, like the good little boy that look reduced him to.

She cleared her throat and addressed the girls, some sitting on the beds, some lounging in other locations and the rest standing, ready for the speech. “I wanted to thank you all so much for being here, and hope you know it means the world to me! Let’s get ready to black out, hoes!”

Charlie giggled, “Always classy, Jo.”

“You bet, cheers!”

Everyone did so, and threw their shot back. It was just as gross as Dean thought it was going to be - but it burned in a _strange_ way and _clung_ to his throat more than it _went back_. He frowned and gruffly asked, “The hell is this?”

“Kinky!” Jo answered automatically.

“Duh, but what’s the drink.”

“Not _you_ , Winchester!” Anna gestured to the bottle, now submerged in ice, “The _booze_. It’s ‘Kinky.’”

“Oh god.”

“Welcome to a bachelor _ette_ party, dude.”

\----------

A few shots in, a couple _fashion shows_ for the girls to decide between outfits, and _makeup touch-ups_ , Dean was starting to figure out what everyone’s name was. He also got burnt by two curling irons, and that's when it _really_ hit him, he wasn't out with the dudes. What was he _thinking_? This was stupid, this was _dangerous_ , these women were like _black widows_ armed with _weapons_ and- but back to the names! Who knows if he was going to remember by the end of the night, but he really _was_ trying. These (as dangerous as they appeared) were Jo’s _friends_ , after all, and he’d be seeing them all again at the wedding. He, _heaven forbid_ , was trying to make a good impression. Plus, if he (being a groomsman) used this as a head start to hook up with one of the bridesmaids after the wedding, that was just the natural order of things, right? Or, if he was lucky and it happened tonight, who cared?

He already knew Charlie, and he was close with Charlie. Hell, Jo knew Charlie _through him_. They’d been close for a long time, and as soon as he’d brought Charlie around and introduced her to the family, the women had instantly clicked. And instantly ganged up on Dean. Oh joy. But, obviously, friend-zoned aside, she loved the ladies, even more than _he_ did - so she was obviously out.

Anna wasn’t a prude, by any means, but she always had that air about her that screamed ‘out of your league.’ She had met Jo when the woman had gone off to school, and that’s the same way she knew Tessa. The two rich girls had taken Jo under their wing, being upper classmates in the same program and had stayed in touch long after they graduated. Still, Dean never thought of them as anything other than ‘Jo’s friends,’ and nothing he’d really be interested in.

Meg and Ruby were wild cards. When Jo had went off to school, she stuck with a job she knew backwards and forwards - bar tending. These two women stayed close to each other, smoky eyes and red lips, whispering jokes the rest of the party wasn’t let in on and _helping themselves_ to shot after shot. Hell, Dean figured the two could watch out for themselves, in those sky-high red-bottomed shoes, they looked the _most_ dangerous. But if they ended up falling _off_ those stilettos he’d need to step in as a babysitter, and pronto. He appreciated their sass, but they seemed more into each other than socializing with the rest of the party.

Bela was also a bartender at the joint Meg, Ruby and Jo worked, and she was much more friendly. Much, _much_ more friendly. To the point that she actually intimidated _Dean_ a little, if he was being honest. Sure, the British accent was hot, and rolled right off her tongue, but her downright sexual innuendos and snappy comebacks gave him a run for his money, and that was saying something. But still… she was a _possibility_. After all, she’d probably be wild in the sack, and all weddings were meant for was a one-night stand for the lonely, not relationships. Duh.

There was a sweet, blonde girl named Jessica, who Dean actually could hold a conversation with. He did so for a while and commented alongside her on Jo’s wardrobe when she was picking out the perfect dress. But after hanging out with her, he realized just _that_. She was way _too_ sweet and sincere. An honest to goodness, kind Midwestern girl who went to high school with Jo. Someone that deserved to be wined and dined, and not just hooked up with for a night. She was the kind of girl that Sammy deserved. He was going to try to get her number by the end of the night, just so they could meet up the next time she was visiting her parents in Lawrence, see if he couldn’t get the two of them together... Or at least break the ice at the wedding?

Speaking of his brother, if he had to listen to fuckin’ Becky Rosen talk his ear off about him one more time he was gonna freak out. This was Jo’s day, not _'I wanna marry your brother and have his sasquatch babies so hook a home-girl up,’_ day. So. Yeah. No. Ew. No.

Another off-limits lady, was Dorothy, who Charlie had specifically claimed ‘dibs’ on in the car on the ride over. She was gorgeous, he could see why Charlie was so taken with her, and Dean could play a fantastic wingman to one of his best friends. He’d made it one of his goals for the night - even though it wouldn’t be _that_ hard. Dean had saw the way Dorothy was stealing glances at Charlie while she was busy putting on her eyeliner in the mirror.

And Hannah... Hannah was too serious. Like... _Really_ serious. And border-line _awkward_. Apparently, much like Anna and Tessa had taken Jo under their wing at the university, Jo had returned the favor, by ‘adopting’ Hannah. What baffled him, was that when she’d first met Hannah, she was even _more_ socially awkward than she was now. Which seemed _impossible_. Dean went out of his way to play bartender to the party, and made sure the woman got _doubles_ of _everything_.

But Lisa... _Lisa_ was something he could _work with_. The woman was smoking hot. All olive skin and dark hair. She didn’t pile on the makeup like some of the other girls, she was just naturally beautiful. And her more humble dress did nothing to hide her slim, but perfectly toned body. She was opinionated, but not brash. Sweet, but not saccharine. In short: she was ideal. How had she been in Kansas this whole time and Dean never found her until now? And how had she been a _waitress_ at the _Roadhouse_ , of all places? It must have been during his road trip phase, when he wanted to be _anywhere_ but home. But, damn, he missed out. Time to make up for lost time, right?

He didn’t want to come on too strong, so he settled on sending her flirty smiles every now and then, which she returned, and that was a good enough sign for him. He was gonna pace himself. It always paid off in the end.

“What are you wearing, Dean?” Jessica asked, and then sipped her drink. “Not that I don’t think you don’t look _lovely_ now, but the dress codes in the places we’re looking to go are-”

“I got it!” Charlie pulled out a garment bag, which also held her dress for the night, “Figured you’d forget, so I took the liberty of going through your closet and finding you something sexy.”

“You’ve _got_ to be kidding me.”

“Lady’s right!” Charlie unzipped it and started pulling out neatly-pressed items, “Dress code. Can’t have you looking all Paul Bunyan out on the town. Plus, you gotta look like you fit in with all these hot bitches here, right?”

“As long as he doesn’t look like a pimp,” Meg snickered, “Don’t want any money getting thrown our way, with questions about blow jobs.”

Hannah looked appalled, and Tessa automatically topped off her mixed drink.

“Yeah, yeah.” Dean looked Charlie’s choice on the bed, and didn’t _hate_ it, so he snatched it, and went to change in the other room.

It’s not like he was self conscious, but a dozen _vultures_ staring at him while he stripped down to his skivvies was not his idea of a good time. Not _yet_ anyways. He needed to leave _some_ mystery for whichever lady he was ‘saving himself’ for Jo’s wedding night. He pulled on the black pants, which he’d probably worn of total of twice in his life, but when Charlie mentioned ‘dress code’ he knew that usually meant ‘no jeans’ and she didn’t have a lot to work with in his closet. At least he was more comfortable in the burgundy button-up, and black blazer which, both, were a little more worn-in. And that’s what mattered, right? Plus, the pants were nicely tailored and his ass looked _fantastic_.

When he walked back to the main room, the remaining girls had taken his exit to slip on their own dresses, and cat-called at his arrival. He rubbed the back of his neck, but did _not_ blush. Okay, maybe he did blush a _little_. But the attention of so many women, solely on _him_? Yeah, that could cause a guy to blush.

“All right, everyone! One more shot for the road?” Jo bent over to grab the last bottle, which happened to be whiskey, and Dean was thankful. Maybe there _was_ a God.

These women could drink their liquor, having gone through a handful of bottles already.

He gagged to think of the assortment he had already consumed, and knew tomorrow he was going to feel it. But at least he was pleasantly buzzed? At - he looked down to his watch - shit, _only 10?_ No big. It was the perfect time to start out, and he could handle a few more drinks when they hit the town, and still perform his ‘duties.’

Hannah, after being spoon-fed ( _spoon-drank?_ ) many a mix, was finally starting to loosen up, and helped Jo pass out the shots. The only one who frowned at his drink of choice was Becky. Of _course_. She struck him more as a Cosmo princess, or something of that sort. But Dean gladly accepted, with a grin. Now that everyone knew each other, they took the time to clink everyone’s glasses together individually, as a promise of a fun (debauched) night ahead.

Dean had never saw so many different kinds and styles of leather jackets in his life, as the majority of the women pulled them on. They looked like a friggen gang. He tried to commit them to memory, because the _first thing_ women tended to forget when they were drunk, was their _goddamn jackets_.

Yeah, he was a good ‘bodyguard’ turned babysitter. _Excellent_ , actually.

“The first place is in walking distance!” Charlie announced, and grabbed a few of the hotel keys, looking around to see who would be the most responsible.

She handed one to Anna, one to Lisa, another (with a shy smile) to Dorothy, tucked one into her own pocket, and then, begrudgingly, handed one to Meg. She took the key with a wink and a smile, as she turned around and lead the group out of the room, then down the hall. Dean waited to take up the rear, and made sure the doors locked soundly behind him.

The girls _fuckin’ strutted_.

And, all right, maybe Dean did feel like a pimp.

But at least all his girls were high-class, right?

\------------

They didn’t call it ‘the Windy City’ for nothing, and as they arrived at the first bar, everyone besides Ruby (who had worn her hair in a sleek updo) was struggle to tame their tresses. Dean could have laughed, but didn’t want to risk getting punched by the pouting women.

The bar was nice. Really nice. An upscale cocktail lounge, with a beefy door-guy who Dean had to banter with to convince he was with the woman who had a reservation, and therefore didn’t have to pay the $25 cover. Jo had backed him up immediately, being way more intimidating, _especially_ in her six-inch heels, than he could _ever_ he. She was the soon-to-be bride, after all. Who _dared_ mess with that?

With the clicking of shoes, they walked up the staircase to an even nicer, dimly lit area, where only a few tables were set up. There was a _giant_ one with a fancy 'reserved' sign sitting atop it awaiting them. It held circular bench seating surrounding the large table with a few candles, and Jo excitedly hopped over to take a seat in the middle.

“This is cute!” Jess announced, as she pulled off her jacket, and hung it on the coat rack next to their sitting arrangements. “Who picked this place out?”

“Yelp,” Charlie winked, “I’m very good with my apps, I’ll have you know.”

“Or anything, technology related,” Lisa added, crossing her legs primly from where she sat. “Always impressed.”

“Plus,” Anna leaned into the table with a grin, “I know the bar tender.”

“ _Know_  or _fucked_ the bartender?” Ruby flicked the redhead’s arm, who made a thoroughly offended face.

“He’s my _brother_!”

“Oh. Oops.” But Ruby looked far from apologetic. If anything, she looked more amused.

“So, where do we get a drink around here?” The British woman asked immediately, which had Dean rolling his eyes and looking over to the bar.

But before he could offer to get the first round, a waiter quickly approached the table, pulling out a pen and paper. With a welcoming smile, he asked, “What can I get you ladies-- and, uh, gentleman, to drink?”

“Aww, he called you a _gentleman_.” Meg snorted, “First time for everything.”

Dean made a face, but then flashed a charming smile and whispered conspiratorially, “See that blonde chick? She’s the bachelorette. Make her the most disgusting, sugary sweet drink ya got. With lots and lots of liquor and-”

“Ew, _Dean_!”

“And I’ll have whatever whiskey you got, on the rocks.”

“You got it, sir. The rest of you?”

The girls rattled off random things, and the man was gone just as quickly as he had come.

“I hate you,” Jo pouted, glaring at Dean. “If I puke from this, you’re holding my hair.”

“Oh, you’re gonna puke by the end of the night, all right. But I’m gonna seriously judge you, if it’s here and now. You’ve still got a long night ahead of you!”

“Seriously, Joanna,” Anna teased, “Maybe we should pace ourselves? A drink an hour or something?”

“Why?” The man frowned, “I thought ya’ll were gonna get ‘white-girl wasted.’”

“Duh,” Ruby rolled her eyes, “But we’ve still got seven more hours. And, shit, how many shots have we taken already?”

“Seven?!” Dean demanded, his jaw dropping, “What the fuck-”

“Never been to Chicago?” A new, mischievous and decidedly _male_ voice asked. “Ya ain’t in Kansas, no more!”

Dean jerked at the proximity of the voice, and immediately grabbed his drink as the bartender from before set it down in front of him. To cover up his embarrassment, and calm his heart rate, he took a chug, and noticed Tessa made way for Anna to sneak around her. She rushed to where the voice came from, and it was only then that he turned in his chair to see the woman wrapping her arms around a man a little shorter than her in her heels. He wore a shit-eating grin that annoyed Dean right off the bat.

“Why, Anna!” He gasped, as she pulled away and he held her by the shoulders, “Don’t you look like a little tramp!”

“Shut up, Gabriel!” She playfully smacked him in the arm, before turning to the group, “This is my dick of a brother, Gabe. This is… everybody.”

“Oh la la,” he rubbed his hands together as he looked at the party, “You’ve got a group of beauts here, don’t ya? And Miss Joanna, you’re looking stunning. Hope you enjoy your mystery drink. Everyone else, yours are _kickin_ ’ too, don’t you worry. And first round’s on me!”

Anna kissed him on the cheek, as waiter set down the remainder of the drinks he was balancing on his tray with expert skills.

Gabe tapped Dean on the shoulder and snickered, “Hope I didn’t make ya piss your pants, Deano. I enjoy the element of surprise.”

“How do you know my name?” He glared, immediately deciding that whether or not this drink was free, he did _not_ like the man standing above him. He looked like an asshole. Even _Anna_ had introduced him as a dick. And that smarmy face…

“Jo said she was bringing a manly bodyguard. Although, you look more pretty than manly, fit right in with the girls.” He wiggled his eyebrows, and Dean’s jaw hung open.

“Are you… trying to pick a fight?”

“Don’t worry, Dean, he’s always like this,” Anna elbowed her brother in the ribs, “Can’t take him anywhere. Which is why they stick him behind the bar. For his cheesy one-liners and bad humor.”

“You wound me, sister.” He put his hand over his heart and sniffed, “Well, _this_ bar closes at 2, at least. But I heard you guys were staying out allll night loooong,” he sang a little melody, “Maybe I’ll meet up with you later, if it’s all right with the special lady over there?”

Jo was too busy making an unattractive face after to taking a sip of her drink to respond. “Blech. _Only_ if you get me something _drinkable_. I think I’m going to die, if I take another sip.”

“Perfect! I was hoping you’d say that!” He cheered, and reached across the table to snatch it away, “I’ll take this, as long as you don’t have cooties, and make you a whiskey and coke. You’re still into that, right?”

“You’re the best, Gabe,” she shot him a thumbs up.

With the straw in his mouth, and under Anna’s scrutiny, he shrugged his shoulders and commented, “You’re judging.”

“You just made that nasty drink _you_ love, didn’t you? _Knowing_ she’d hate it, and you could get it for _free_ , while on the job?”

“What can I say, can‘t let a masterpiece like this go to waste. I _always_ have a contingency plan,” he winked, and shook his hips as he finished the drink, and walked back to the bar.

“Anna?” Dean looked up at her with a blank expression. “I don’t think I like your brother.”

She nodded with a solemn stare, and confirmed, “He’s an acquired taste.”

\-----------

Okay. Maybe Dean _had_ acquired a taste. Because, one drink ‘on Gabe’ had turned into _four_ , and the pleasant buzz everyone had been feeling when they had arrived at the bar had turned into drunken fuzzies, laughter and a little skip ( _stumble_ ) in their step.

A little after midnight was when Gabe's shift ended, and they finally made their way out of the lounge. What Dean did _not_ expect, was Jo willingly, and excitedly going along with the man’s idea of where to go next.

Which _happened_ to be a gay bar.

Dean groaned, because _this_ was what separated bachelor and bachelorette parties. Instead of a strip club, they went to a goddamn gay bar.

Not that Dean was homophobic, or anything, but he never understood why girls _loved drag queens so much_.

Jo’s arm was looped through Gabe’s as they took the led, and Dean had to smile to himself because right behind them was Charlie, who was heavily leaning on Dorothy. She did not seem to mind in the _slightest_. He didn’t even notice Meg come up from behind and wrap an arm around his waist until it was too late.

He jumped.

Why was everyone scaring the shit out of him today!?

“Aww, Deanie. Did I alarm you?” She wasn’t slurring _per say_ , but her drawl was more _pronounced_  and her expressions untamed. “Didn’t mean to. Just wondering how our big bad bodyguard’s doing. Ruby and I‘ve been trying to figure it out.”

Dean frowned at her words, “Figure _what_ out?”

“Which team you’re batting for. Perfect spot to find out, wouldn’t you say,” she gestured to the marquee of the place Gabriel had claimed as their destination.

“What?!” The words were out of his mouth before he could stop them, and he hated it but he sounded… defensive.

“No need to play coy,” she stroked his arm, and then nuzzled a bit. God, maybe she _was_ pretty damn drunk. “I’ve saw you check out _just_ as much dick as tits tonight.”

Obviously, her partner in crime was within earshot, because he heard Ruby cackle from behind them. Which left him gritting his teeth.

“What’s it to you, anyways?”

“It’s nothing to _me_ ,” she smirked, “Like I said, just trying to figure it out. And we’d like to repay you for all your hard work, watching us little girls tonight. So, what’s it gonna be? We keeping our eyes out for a lovely lady or a stud?”

“Wait.” And then it dawned on Dean, “You’re trying to set me up?”

“Duh,” she rolled her eyes. “It’s fun. On nights like this. Obviously, Ruby and I are going back together, and you intrigue us, let us help.”

“Wait-” Dean nearly faltered in his step. “You two are-?”

“Another, _duh_ ,” Ruby repeated her, apparently,  _girlfriend’s_ words, and came up along the other side of Dean. “You’re not playing nice with us. When do you have two hot chicks offering to wingman you?”

“Uh…”

“Very eloquent.” Meg pulled out a pack of cigarettes as they filed into the decently long line at the door. Ruby snagged one immediately, but when she offered one to Dean he politely declined.

Both women were still looking at him as though he were _prey_. He couldn’t help but fidget on his feet. They were kind of _terrifying_. And now that they had made him their pet project, that was as good as sinking their teeth into him. No matter what, he was fucked. Which was why, he had _no idea_ how the next words tumbled out of his mouth, even if they were little more than an unsure guess.

“Both... I think?”

The two exchanged devious and _delighted_ looks, before Meg pulled out her lighter and winked at Ruby, “Ahh, the options are endless! This will be fun.”

“Somehow, I don’t think our ideas of ‘ _fun_ ’ are even in the same _realm_.”

After taking a long drag of her now-lit cigarette, and blowing smoke into the air, Meg leaned into him and whispered, “Oh, but it _will_ be.”

\------------

Once everyone’s hand was stamped, and they walked into the club it was a fucking _free for all_. The girls _scattered_ , and Dean didn’t even know which way to go. Some ran to the bar, others the bathroom to ‘touch up’ (which Dean _obviously_ couldn’t follow them to) and others, upon hearing the pounding base, shrilly announced, “OMG this is my song!” and disappeared onto the dance floor.

Dean was left frantic, like he was facing a fight, because he hadn’t known many of the women long enough to know what their tolerance was. Who was the most likely to black out first? Were any of them ‘that girl’ who ended up crying in a bathroom stall, because of an earth-shattering drunken crisis over nothing? He felt the pull of duty, because when he was drunk, and given a mission, it was all or nothing. And, dammit, if he hadn’t already grown attached to the majority of these chicks.

Turns out, he wasn’t given an option, as Jo grabbed his wrist and pulled him to the bar, where Hannah, Ruby, Meg and Jess were divvying out yet _another_ round of shots.

And, _damn_ , Hannah was really _gettin’ it_ , unbuttoning her too-high collar, letting a little cleavage show and swaying (off tempo, mind you) to the beat of the music.

Now that he had found of few of them, Dean’s eyes surveyed the dance floor, and was happy to see that Gabe was with a group too. He was also ’backing that ass up’ on Becky, who was blushing a vibrant red. Yep. Dean definitely liked the guy now.

A shot was in his hand, and the glass clinked before he could turn back around. He caught up, once the girls were throwing theirs back, and after doing the same, hissed at the taste.

Hannah, of all people, _shoved_ a lemon in his mouth to chase the burn of the damn tequila, since he _obviously_ hadn’t gotten the memo.

Dean nearly choked on a seed, but thanked her, and received a pat on the head for his efforts.

Everyone was muffling their laughter at the woman’s clearly glazed over look, but she was having the time of her life. Dean didn’t fault her for it.

He _did,_ however; fault _Meg_ , when she pinched him on the ass, and announced, “Rubes and I are going ’hunting’ for you. Be back in a jiffy.” Then, they disappeared into the crowd.

“Hunting?” Jessica raised an eyebrow, with as smirk of her own, “They gonna bring you back a deer, or something?”

“More like a bronco.” Jo snorted.

“Shut up!”

\---------------

Dean _didn’t_ dance.

It was a simple fact of life.

However, intoxicated women, who didn’t take no for an answer, were also something he didn’t take into account when the book about Dean’s life was written.

Which was how he found himself on the dance floor, crammed in between the sweaty bodies of his friends, strangers, and covered in glitter.

Lots and lots of glitter.

At least, he was drunk now.

He could _only hope_ he was drunk to the point that he could block this out of his memory tomorrow and pretend it never  _ever_ happened.

_Especially_ , the part about him _enjoying_ himself.

He twirled Charlie around, dipped Jo when she shimmied her way over to the sound of Iggy Azalea, and even found himself teamed up with _Gabriel_ in a _dance battle_ against two other dudes (covered in fuckin‘ _body paint_ ) at one point. Meg and Ruby were pointing out some hot guys around the club at random, but no one was catching his eye, and he wasn’t about to leave the group for _just anyone_ battling their eyelashes.

However, some girl in the corner (strangely enough) bought him a drink and with one wave of her hand, had him _there_.

_Okay_ , he _admitted_ , it was way easier for him to get pulled in by a woman. Even if he _had_ confessed a mutual attraction of men and women alike, this _was_ his comfort zone. He _knew_ how to flirt with a chick, he could do it in his _sleep_ , and the way that the red dress hugged her curves was _too_ tempting to say no to. Oh, and the free drink helped, of course.

When he approached her, beer in hand, he put on a winning smile and casually asked, “What’s a girl like you doing in a place like this?”

Normally, that was cheesy as hell, but in this case:  _applicable_.

She smiled back and boldly traced her fingertips along his forearm, visible from having rolled up the sleeves on his blazer in the heat of the club. “I’m here with some friends, like you.”

“Yeah? Where’d they run off to?” He took the empty bar stool next to her and sipped his drink.

“They’re upstairs, seeing what the party’s like there. I’m waiting for a text to see if I should venture up and join,” she gestured to her shoes, “Unfortunately, I overestimated my ability to walk in these babies all night. Stairs are _not_ worth it if the scene’s lame, you know?”

“Can’t say that I do, but I already know two of the girls in the bachelorette party I’m chaperoning have taken their’s off,” he winked, and then dramatically shuddered, “But they’ve chosen their fate. Hope they don’t catch something from the floors, or sidewalks.”

She threw her head back and laughed, “Right. Brave women!”

“Very, very brave.” He confirmed, “So, just wanted some company…?”

“My friends call me Abby,” she extended her hand, and then looked a little coy. “And I was hoping you could do me a favor?”

“I’m Dean,” he shook, and let his grip linger, “And, of course. Name your poison.”

Her eyes lit up, and she continued, “So, there’s this girl here. She seemed nice at first, bought me a few drinks, but she’s getting really, _really_ aggressive. I tried to explain to her I was here with friends, and I was straight, but she _won’t_ leave me alone, and it’s starting to bug me. Could you pretend to be my boyfriend?”

“Huh,” Dean cocked his head to the side, but nodded, “Yeah, yeah, I can do that. What’s this girl look like?”

“Like that,” she jerked her head, and sure enough there was a fiery brunette, _coming in hot_.

Her eyes were narrowed as she looked at Dean. They narrowed further, as Abby snuggled up against him, and he wrapped his arm around her waist. “What’s going on, Abby?”

“This is Dean,” she toyed with one of the top buttons on his shirt, “I’m going home with him tonight, so you can find someone else. Isn’t that right, love?” She titled her chin up and gave him a smile.

The man opened his mouth to say something, but the other woman who had just charged over, easily interrupted him.

“You cheating _bitch_!”

And not _only_ was Dean _splashed in the face_ with a mixed drink that left his _eyes fucking burning_ , but the glass holding it  _shattered_ on the wall _inches away_ from Abby’s _head_.

The redhead on his arm was quickly gone, as she shoved off Dean, which nearly had him falling on his ass, and roared, “ _I’m_ the cheating bitch?! What about _Lilly_? And _Cheryl_?! You have no right to-”

And right before Dean’s eyes, the brunette grabbed a _fistful_ of Abby’s hair and whipped her into the wall.

He jumped out of the way _just_ in time to avoid being body-slammed, as Abby fought back, and clawed at the woman who (to Dean’s best guess) was her _girlfriend_?

Dean had been _played_.

He was standing there, dumbfounded, staring at the mass of kicking and screaming limbs as the women screeched and rolled on the floor.

“Uh... Security?!” He responded, a little too late, because requested men were _already_ pulling the two off each other.

“Don’t even pretend you like dick, Abby! We both know how much you love pus-”

“You’re lucky I didn’t rip that tacky fucking weave out, you cun-”

“Dean!” Charlie was running up to him, as Dean continued to _stare_.

Both women were bleeding from random scratches, with blooming bruises, and the brunette with a black eye. They were scrapping against the security guards on their way out, and another security guard was approaching Dean.

“Charlie, I have no idea what just happened…”

She glanced around to survey the scene and shrugged, “I’m just glad _my_ breakups have never been that bad. Chick’s can be _vicious_ , dude.”

“Uh, yeah. Seeing that now. Fuck. I need another shot, or two.” He shuddered, wiping the sticky reminisce of the projectile mixed drink from his face and b-lining for the bar.

Meg appeared out of nowhere, signaling she wanted a drink too alongside Charlie, then leaned across, “See why you need a _man_. Women are _crazy_.”

Both made eye contact in a silent confirmation, and all three, in unison, threw back their drinks.

\-------------

By the time they left the club, it was edging on 3:30. Gabriel knew of one other place that was worth it in the area _and_ was open until 5. It was an after hours piano bar, and everyone was _more_ than happy to wind and spend their last little bit of the night in some place less... _Hostile_. Well, not _quite_ everyone.

“ _Baaabyyy_ , can we just go back,” Ruby whined against Meg’s shoulder.

Well, it wasn’t _really_ her shoulder, since she had taken her heels off, and Meg still had hers on. It was more like she was whining into her breasts. Meg, god bless her, was drunk, _sure_ , but she was still keeping up with the group and running her fingers through Ruby’s hair.

“All right,” Meg halted where her girlfriend was stumbling, and the rest of the group turned around. “Who wants to call it a night right now?”

More than half the hands shot up, Dean’s included. Charlie quickly slapped his down.

“Ow!” He hissed at her, “The hell, Char?”

“You’re the _bodyguard_ , and we need you now more than ever,” she started, like it was obvious. “Don’t let some gay sudden death match get you down.”

He huffed, but went along with it.

Hannah hadn’t raised her hand, but Ruby grabbed her anyway, knowing she’d be dead in a ditch (no matter how _awesome_ Dean’s babysitting skills were) by the end of the night if she didn’t go back to the hotel _right then and there_. Becky, Tessa, Bela and Lisa joined the huddle, and that’s when Meg reached out and hailed a cab.

The driver rolled down the window and looked at the group before yelling out, with a heavy accent, “I can only take four.”

“You’re taking six, _buddy_ ,” Meg leaned through the window, showing off an _obscene_ amount of cleavage, along with a $50 and winked, “They’re small girls, they can squeeze. Or sit on laps. Just get them back to the hotel safe and sound, and you can keep the change, yeah?”

“ _Six_?” Ruby stomped her foot, suddenly regressing to childhood, “ _You’re_ not coming, babe?”

“You’ll be fine, still gotta get Deano a _catch_ ,” she opened the door for her girlfriend and kissed her lips quickly, “Besides, you gotta claim one of those beds for us, all right?”

“Okay,” she finally resigned, and scooted into the cab, “Looooove youuu.”

Everyone else piled in, as the woman blew her a kiss, and soon they were off.

Dean blinked at her before groaning out, “Coulda gone back with her. You’re _not_ hooking me up, Meg.”

“Ship’s already sailed,” she opened her arms widely, and barely stumbled as she walked back, “’Sides, I want a little cool down and a cordial to cap off the night.”

“Yeah, yeah.”

Gabe snickered, and grabbed his sister’s hand, “And then, there were eight. Huh. Still a huge number. Where’d you get all these friends anyway, Jo?”

“The world will never know,” Jessica teased, poking Jo in the side, who was looking a little glassy eyed.

“Shaddup, ya’ll love me.”

\-----------

The piano bar had a nice ambiance. There weren’t a lot of people, and those who were left were kicking back, and relaxing at the end of a long night. Some people were in suits, others were hipster kids, but no one looked _quite_ as plastered as the group who just wandered up. Anna was beginning to hiccup as she pushed through the doors, and presented her ID to the bouncer, who raised an eyebrow, but didn't turn her away.

“One more shot for the road?” She grinned, and ran right to the bar.

Earlier in the night, everyone would have _rushed_ to follow her, but now the pace was winding down. Eventually, everyone made it at _different_ speeds. Gabe was right up next to his sister, as she was leaning against the bar and ordering eight shots of jager.

“Jager?” Jo felt her stomach roll over, “For the road, Anna?”

“It’s a _cordial_!” She defended, looking at her wide-eyed, “That’s the section it’s listed under atta grocery store!”

“Oh _god_ ,” Charlie lulled her head against Dorothy’s shoulder, and the other woman laughed.

Dean, while he made a face, wasn’t mad about it. _Yep_. He was _drunk_. But he could handle _one_ more shot.

Probably.

_Maybe_.

Okay, hopefully _Gabriel_ would be a better bodyguard than him, because he couldn’t guard _himself_ right now, if his life depended on it. Let alone anyone else. Gabe winked it him, knowing his exact train of thought, as he handed Dean the dark liquid. Yes, Gabriel was in much, much better guarding condition, if anything called for it. _Good_. Dean could _finally_ let loose. He toasted the women and other man, and got a chill as it rushed down his throat. Ugh. Maybe that _wasn’t_ the best idea. Tooooo late.

He looked down to the bar, and noticed there was _one_ shot glass that remained _full_ , but everyone around him was wearing similar faces of disgust, so he wondered who the last one belonged to. As he counted his friends, one _was_ missing. And it was _Meg_. He snatched up the glass, and turned around to find her.

He walked around the bar top, and caught sight of her from the other corner, but she was with someone else. He raised an eyebrow as he approached, the way she was leaning over and chatting away, was blocking the stranger from view. He tapped on her shoulder from behind, and she turned around with a smirk.

“Hey,” she cooed.

He pushed the shot into her hand, and joked, “You weren't there for our last toast of the night. Rude, Meg.”

“Aww, thanks for bringing this over, sugar,” she winked, and tossed it back, “Such a gentleman.”

It was only then that she leaned back, and Dean got a good look at the man she was engaging in... whatever she was engaging him in.

_Whatever_ it was, _Dean_ wanted to _engage_ , too.

He looked rumpled, like one of the businessman after a long night, but he was _way_ too hot to lump him in with those geezers. His five o’clock shadow had grown in, Dean mused, because it was coming up on friggen _5AM_. The tanned skin and muscled expanse of his forearms showed from where his jacket had been rolled up, and _fuck_ , those were _nice hands_ , and his grip was wrapped around a sweating beer bottle and Dean wonder what else those hands could do... _Damn liquor._ His dark brown hair was tossed in the _perfect_ messy way, Dean could feel himself drooling, because those _eyes_ … _dammit_ those _eyes_ , were the most vibrant, perfect shade of blue he’d ever saw.

“Castiel, this is my friend Dean, Dean, this is Castiel.”

“A whut-?”

“Castiel.” Was his cold response, like he’d dealt with it many times before. “My _name_.”

“Oh, uh, sorry dude.”

Meg rolled her eyes. So much for first impressions.

“Castiel was just talking to me about how this was his first time in Chicago. This was your first time too, right?” She prompted, raising an eyebrow.

Oh. _Oh_. Maybe _this_ was her last ditch effort to hook him up with someone? _Yeah, right_ , this guy was way too sexy, sober, and obviously _unimpressed_ for his own good.

“Yeah,” Dean cleared his throat, “I mean, first time _partying_ here, I’ve driven through here before. What about you?”

Then he smacked himself, because _that’s what Meg had just said_. He tried to backtrack, and stuttered out, “Well, you said it was yer first time, I _mean_ did you party, or…?”

“I’m here for my job.”

“Oh. Cool.”

Meg kicked him under the table in the shin. _Hard_.

He yelped, and attempted to recover by raising his hand over to the bartender to flag him down. Thankfully, the man was quick, and the tap was right in front of him, so there was a glass in Dean’s hand to drown his idiocy _right away_. And _Meg_ was talking to the guy, _easily_ , and he was _jealous_. She looked over her shoulder and glared, “ _Dean_ , come smoke with me, yeah?”

“Yeah.” He squeaked.

“There’s a patio,” Castiel stood up from his place at the bar and waved Meg to follow, "It’s warmer than going outside."

When he began to lead the way, Meg hissed under her breath, “Why’ve you suddenly gone _stupid_?!”

“ _I don’t know_!” He kept chugging the beer, now half gone, “I lost my _fucking_ _brain_ somewhere after 3am _all right_?!”

“Now’s the time to get it back!”

Castiel was holding open the door, which Meg thanked him for, sat down on the patio furniture and pulled out her cigarettes. Dean snagged an ashtray, and set it down in between then, as a silent _plea_. By now, Meg had tuned into Dean’s wave length, and handed him a cigarette, as well as her lighter, as soon as she lit hers. It took him three times to light the damn thing, and take his first inhale. And _shit_ it’d been a long time since he’d smoked, because the first hit left him a little _dizzy_. But _thank god_ he didn’t cough. Because that would have left him _mortified_. Fucking _amateur hour_.

“So, Russian?” Meg purred, and Dean wanted to snap at her that she was _his_ _wingman_ and to stop flirting, but he was doing a shitty job of being _winged_ , so it was a moot point.

“Wait, you’re from Russia?” Dean echoed, suddenly intrigued, “You don’t have an accent.”

“She’s commenting on my last name. I’ve been in the States for a long time, I merely conduct business there from time to time,” he explained, leaning back on the chair and crossing his legs. “This is a bachelorette party, correct? What are _you_ doing here? You‘re clearly male.”

Dean was put off by his tone, and felt his mood turn from enamored to snappy, “Clearly,” he scoffed. “ _All_ male.”

“Put it away, Dean,” she smacked him lightly, but it was a silent order to _shut the fuck up_. “The bride’s his best friend. And it was a _massive_ group of girls,” she exhaled a cloud of smoke before finishing, “He’s done a marvelous job of making sure we’re on our best behavior tonight.”

“I thought the whole point of these celebrations was to _not_ behave.” The blue-eyed man bantered with Meg, but his eyes flickered to Dean, for a split second. “Your job is unnecessary.”

All right, _now_ Dean was getting some _serious_ mixed signals. Was that a jab? Was that him _flirting_? Was he flirting with _Meg_? Was he mocking _Jo’s_ decision? _What the actual hell?_

Dean’s mouth moved faster than his brain, and out came, “I’m making sure _they_ behave, not _me_.”

Meg finally beamed at him, in her own, impish way, and tacked on, “Someone needs to watch Dean, most of the time. He can be naughtier than the girls.”

“Interesting.” Castiel’s attention was no longer on either Meg nor Dean, but rather down to where he was picking at the label of his beer bottle. “Perhaps I can buy the bride a drink?”

“Hah,” Dean killed the cigarette when it was a little more than half done, “If she’s still vertical, maybe.”

“If not, I suppose you could drink it,” he finally lifted his eyes from his drink, and met Dean’s gaze.

“Y-Yeah. That could work, too.”

“Let’s go inside, shall we?” Meg said in a sing-song voice, as she snuffed out the end of her own cigarette. “Hopefully, Joanna is still alive.”

\--------

The three walked back in, just in time to see Gabe waving at everyone, and announcing he was getting Anna back to the hotel room. Which was good. Because she was two seconds away from rag-doll status, hanging from his arm. Dean called back to him, “Make sure she makes it to the toilet!” to which the redhead raised him a middle finger, and they were off.

Jo and Jess were giggling at the bar, pointing to where Charlie and Dorothy were _straight-up making out_ in a booth in the corner. Dean winked at Meg and jerked his head to where the women were, “Looks like you are Ruby have some competition for cutest couple, huh?”

“ _Please_ ,” Meg rolled her eyes, “It’s not even a competition.”

The newcomer tilted his head, and asked, “Are they with you?”

Dean laughed, “Yup. Bridesmaid porn, for everyone’s viewing pleasure, apparently.”

“Get a room!” Jess tittered, and that was when the two parted, and looked thoroughly embarrassed.

Charlie glared, and started digging through Dorothy’s pockets, until she produced the hotel key she had given her earlier. “Ya know what... I think we will!”

“Have fun with that.” Jo shooed them, “Remember the bed I called dibs on, neither of your asses better be parked there when I get back!”

“Oh dear,” Jess leaned heavily against the counter, “Can’t take them anywhere, can we?”  But when she looked back, they _hadn't_ left, they'd _tripped_ over each other in the booth and were laughing in hushed whispers. Guess they weren't going to make it to a cab without assistance, after all.

“Joanna?”

The blonde turned her head to the new voice, and raised an eyebrow, “Uhh, yeah?”

“I’m Castiel,” he smiled, dashing as hell (Dean was annoyed even _more_ now), “I was wondering if I could buy the lovely bride a drink?”

A wide grin spread across her features, albeit, _sloppily_ , because she was ‘blacked out’ as she announced earlier, which made Dean twitch because, _why the hell was she accepting_?! Did she _want_ to die of alcohol poisoning tonight?

“How about you, miss?” Prince _fucking_ Charming then asked Jessica too, who, _of course_ , accepted. Who could say no to _him_?

Dean wanted to bang his head against a wall. But in the middle of his internal struggle (rage) he barely noticed the drink that was put in his hand, until it was _there_. He blinked up, to catch Meg nodding at him, and Castiel smiling.

“Uh... Thanks. You didn’t have to-” Dean noticed how the man’s hand lingered while handing him the beer.

“It would’ve been impolite of me to only get a beer for two, so I decided it’d be best to get everyone a round,” he explained, and noticed Meg had a one in her hand too.

“Nah, really, I was about to call it quits anyway, even if it’s nice’a ya-”

“You and Joanna.” Castiel stated, never breaking contact. “It would’ve been impolite of me to buy only _you two_ drinks.”

Dean’s eyes widened slightly, as he _finally_ understood what the man was say. “Oh. Right. Shit, thanks.”

“Are you always so eloquent?” This time, Dean _knew_ he was trying to bait him, but, _hell_ , if the dude was going to buy him a _goddamn drink_ , why not give it to him right back?

“Only around Russian smart asses.”

“That’s good to know.” He nodded slowly. “Cheers?”

Thankfully, Cas had himself a fresh beer as well, so it didn’t matter when Dean chugged half his right off, because the other man seemed to be keeping up. It was amazing, how quickly he seemed to join the little group they had left. Jo loved him, right off the bat, but then again, Jo loved _everyone_ right now, she even got cozy with one of the _light fixtures_ at one point. Meg dared Jessica to dance on the bar, and thank god, Cas had helped Dean in his role of ‘keeping the girl’s behaved,’ because it took _both_ of them to keep her down. The girl was much stronger than she looked.

Jo claimed Cas was no where near their level, convinced him to 'prove his loyalty to her bachelorette party,' and do a few shots, which the girls joined in and threw back water as a substitute for liquor. He obliged. Dean only took one more shot with him, because his head was spinning, and he kept gravitating closer and closer to the dark-haired man. Thankfully, he didn’t seem to mind.

_At all._

He kept sending him those cute little grins, and eye rolls that had Dean’s heart beating out of his chest. Still, he wasn’t sure if he was just being a condescending asshole, or if he was hitting on him. He was being so kind and gentleman-y with the girls, did he just dislike Dean, or was this to keep him on his toes and...? He had _no idea_ what to think. But he visibly deflated, as the bartender told them it was coming up on last call.

The girls were fifty shades of trashed, so they passed but when Cas raised an eyebrow to see what Dean was going to do - he ordered one more beer. So the other man ordered one more beer. Fuck it.

Jo was blowing bubbled in her water and Meg was telling an offensive, but hilarious joke when Dean felt a warm hand appear low on his back.

“Do you want to go to the patio before the bar closes?”

A shiver ran through his body, but Dean tried to keep it from physically showing. Instead, he tried to play it cool, and appear cocky with it, “I’d say buy me a drink first, but I guess you did.”

With a glance to see the other girls were immersed in Meg’s extravagant storytelling, Dean followed close behind Cas, back to the first place he’d made an idiot out of himself. At least this time, he was a little more comfortable, and had the beer to fall back on. But no Meg. Which he kind of needed. Shit.

The door closed behind Dean, and he plastered on a smug expression, even though he was feeling anything _but_. Fake it til you make it and all. “So, Cas. You, me, the patio. You gonna ask me if Jess is single, or some kinda other girl talk?”

Cas calmly took Dean’s drink out of his hand, along with his own, and set it on the side table.

_Great_. Dean thought, now he didn’t even have _that_ to fall back on if-

Then his backside thumped against the brick of the building and Cas was on him. Like, _really_ on him.

It was a clash of lips and teeth, while one of Cas’ hands cradled the back of Dean’s head so he wouldn’t bust his skull open on the wall, and the other was wrapped around his waist. Dean’s brain was short-circuiting. Did he _die_? From all the drinking? This was too good to be true, this was-

A sharp nip to his bottom lip made him hiss out, and _that’s_ when he realized this was _most definitely real_ and he needed to get with the program. Like, _yesterday_.

Finally, his arms were working, tangling around Cas, trying to pull their bodies closer. Everything was desperate, the way their tongues were fighting, the way their hands were grabbing like they just couldn’t get close enough. Dean was already breathless by the time Castiel’s grip shifted to his hips to hold him in place, and grind against him. He moaned into the man’s mouth, and tried to roll his pelvis, only to be held even _firmer_ _against_ the wall.

His shoulder blades were digging against the brick, and the _friction he_ _wanted_ was against his _cock_ , not his _back_ dammit, but Cas was playing games, not allowing him to move. He could feel the asshole grinning, and swallowing his whimpers as he rutted against him again. All right, maybe not being in control was a secret kink Dean didn’t know he had because he was about ready to cum in his pants after being humped against a damn building.

“Cas,” he shifted just enough to latch onto the man’s neck and suck.

And the delicious moans he got from that was well worth it.

But that was when Cas pulled away.

Dean wanted to chase after him, but they could both hear the clatter of chairs and bar stools being put up on tables. The place was shutting down, and someone was going to come yell at them any time now. Still, that didn’t keep Dean from drinking in the delicious sight of a very aroused, very debauched Castiel. It took every ounce of will power he had to keep himself back.

“Fuck.” Dean closed his eyes and clenched his fist, to ram it into the wall behind him. He needed to get a grip before he walked back in there, he needed to-

“Okay.”

“Huh?”

Cas huffed a laugh, but with a fond smile, “You’re quite dense, Dean.”

“You’re playing hard to get, Cas.” He countered, and walked forward to snatch his beer off the table, before meeting heated blue eyes. “Well, uh, before now... That is. Was. Whatever.”

The other man actually _laughed_ , when he walked over to pick up his own drink.

It was a beautiful sound. Dean had to take a sip of his drink before he word-vomited and told the man in front of him. Said beautiful man approached him in cautious steps, before he reached out and let a hand linger around Dean’s waist.

His voice was hushed, and _sexy as fuck_ , as he asked, “Come back to my hotel with me?”

Dean didn’t even have to think, he just nodded. He would have nodded until he head fell off. But then he remembered and cursed himself, “I gotta watch the girls, though. Make sure they‘re safe.”

“We can take them to their hotel,” Cas leaned in just enough for his breath to tickle Dean’s ear, “Then, after you get them to bed, I’m taking you back with me and fucking you raw.”

“Cas,” Dean whimpered, hating his voice for giving him away, “You can’t just _say_ that shit.”

“I’m not just ‘saying.’ I plan on _doing_ ,” he nipped Dean’s earlobe, earning even more of a whine from the other man. “Shall we get the girls back sooner rather than later?”

Cas went on ahead, leaving Dean to take some deep breaths in, trying to regain his composure. Or whatever composure he had left. Which wasn't much of anything, now that he thought about it. He glared at the drink in his hand, and chugged the rest in record time. This man was going to be the death of him, he was already sure. He had to be the devil in disguise. How he’d managed to charm all these girls, was beyond him.

Finally, after he was sure his erection was under control, he marched back join the group. And prayed he made it out of tonight alive.


	2. Chapter 2

With a sharp stab of pain in his side, which turned out to be _Meg_ unceremoniously _digging_ in her _elbow_ , Dean yipped. Then glared. A very, very intense glare... Which did nothing, but make the woman smile even _wider_. 

“Soooo. You look sexed.”

“Sexed? The fuck is that even supposed to mean!?” He hissed, trying to make his voice low enough to keep Castiel from turning around and seeing him. “What’s he doing?”

She _smirked again_ , which he’d come to find out was Meg’s default face setting. “Paying our tab. Such a gentleman. You could learn a thing or two from that sexy man.”

Dean was nearly certain, if Meg were a man, he would have smacked her by now. Or kicked her. Or dumped a drink on her - something more passive-aggressive (he may _still_ have had time for that, actually...) _However_ , he _had_ to refrain. So instead, he stood there, shifting from foot to foot, as the rest of the party mingled, and Cas signed the receipt he was handed. So, obviously, there had to be a comment from the peanut gallery. Who happened to be from the chick he was trying to not to accidentally kill.

“Antsy, much?” She wrapped an arm around Dean's middle, maybe to get him to stop moving, maybe because _she_ was beginning to tip over herself, “Does he make your panties wet, Deano?”

“I’m pretty sure I hate you.”

“I'll take that as a yes. Aren’t you glad I introduced you? Told you I’d find you a hottie. Now the _real_ question,” she leaned in towards his ear, “Who’s topping tonight?”

“How do you even-?!”

“ _Please_. It’s written all over your face you’re going home with him. I’m not an amateur,” she rolled her eyes, like it was a great effort, “You wouldn’t be this nervous if you were coming back with us girls. So. You gonna ride it, cowboy?”

“You’re-”

“Come ooon, or they’re gonna kick us out,” Jo whined, and added a quick stomp of her (now bare) foot to emphasize her point. Then, she opened her arms and flicked her wrists. “Bodyguaaaard. I need a hand!”

“A hand?” Dean repeated, and walked over to Jo immediately, because it was a great chance to get _away_ from Meg.

He knew he was blushing, as he walked by Castiel, who didn’t even bother to hide the fact that he was currently undressing him with his eyes. And _fuck_ if Dean didn’t want him naked _right_ the fuck _now_.

“Or instead of your _hand_ -” her expression changed to a devilish grin, as she wrapped her arms around his neck and _swung herself around_ to straddle his rear. “Your back!”

“The fuck!” He was almost knocked over from the unexpected weight, but quickly righted himself and hiked her up. “I hate you all.”

“You loooove me,” she nestled her head in the crook of his neck and placed a sloppy kiss in his hair.

Great, now he’d have to wash off _drool_.

“Jo, I can see your vagina!” Jess slapped her on the ass with an impressing 'twacking' noise - which made the girl yelp. “So can the rest of Chicago!”

“Then it’s a good thing I wore my cute undies tonight!” She shook her ass from where she was getting her piggy back ride, until the other blonde took pity on her drunk friend and tucked her own jacket around Jo’s hips to cover her dignity. “Jess…” she slurred out, “I just love you soooo much. Everyone! Have I mentioned how much I love ya’ll lately?”

“And we’ve reached _that_ point in the night!” Charlie groaned, and nearly tripped on the door step as they walked into the empty streets.

Dorothy helped her regain her footing, while Meg cackled loudly at her, pointing like a child on the playground. Dean found himself snickering, despite himself, and wanting to see where Cas was. If there wasn’t a 100 pound weight on his back. He had a duty to keep the bride-to-be alive, after all. It wouldn’t do anyone any favors if they tumbled into the street now and got hit by a bus. And _that_ would be Dean’s luck.

Before he had a chance to ask for the man, he saw the tousled mess of hair outside his peripheral vision, and cursed the fact that _Meg_ was walking along side him and chatting. God, his stomach was doing _flips_. She _couldn’t_ have been saying anything _good_. He wanted to snap at her to get away from his man, but Jo was too busy cooing and nuzzling how 'happy she was they were friends' and 'how much she appreciated him blah blah blah' in his ear. So he couldn’t even hear what bullshit Meg was telling Castiel.

If someone was going to ruin his chances and get Cas to change his mind, it was _her_. Fuck.

Soon, they’d managed to flag down a taxi with enough seats to safely ( _barely_ ) fit them all, and Dean was tossing Jo into the back, followed by Jessica. Charlie smooshed in next to her, pulling Dorothy in with her, while Meg and Dean took the bucket seats, and Cas took the front. Apparently, he was awesome enough to get the hotel information from Jo before she started toppling over, because he was directing the driver where to go. Dean found himself smiling like an idiot over it, until Meg poked him in the side, twice.

Then his good mood was _gone_.

He whipped his head around, and narrowed his eyes, “You better not be cockblocking me.”

“Oh, on the contrary, my dear,” she winked, as she slowly slipped from where she was leaning against the window. “I’m been telling Clarence how much you want his cock _in your_ block.”

“I really hope you didn't say _that_ , because that doesn’t even make sense!”

“ _He_ seemed to get it,” Meg kicked her legs up, one at a time, until they were crossed over Dean’s lap. “And he’s ready to cock you.”

“I’m too drunk for your drunk right now.” He wanted to dig himself a hole to crawl in and die.

Dean also knew Cas could hear _every word_ , because he snorted, and shook his head from the front seat. Apparently, both Dean and Meg had forgot how to control the volume of their voices. Or just _lost_ the ability. Whatever it was, it didn’t matter anymore, because Dean was _mortified_.

“Ahh! Turn up this song, it’s my fave!” Charlie announced from the backseat, already dancing, and the cab driver did just that.

_Thank god_. At least now, Dean didn’t have to talk to Meg and embarrass himself further. Into the chorus of ‘Charlie’s fave song’ there was a loud _thump_ on the ceiling. When Dean looked back, Jess was nursing her hand, looking like she'd swallowed a lemon. A taxi dance party gone wrong. Dean couldn’t help it, he started cracking up, which earned him a sock in the shoulder with her good hand. Even Meg was kicking her feet along to the beat, but didn’t injury herself in the process. _Dammit_.

Before they knew it, they were pulling up in front of the familiar doors to the hotel, and Jo was nearly passed out.

Meg reached back, to grab her wrist and pull her, encouraging her with a gruff, “C’mon champ.”

“Deaaan,” she groaned, flopping her arms lamely, “Piggy, piggy…”

“You calling me fat?” He teased.

She shook her head, which actually looked more like lulling it from side to side. “Baaack. Piggy backkk.”

“He’s giving someone _else_ a piggy back, Joanna,” Meg turned downright _malicious_ again, and snickered, while pulling the blonde through the bucket seats. “Let’s get you to bed.”

“Who?!” She demanded, standing up _just_ enough to _smack_ her head on the roof of the cab. “Oww. But I wanted the piggy…”

“Sorry about that, Miss Harvelle. I promise to return him,” responded a gravely voice.

Fuckin’ Cas, the sneaky bastard, had hopped out of the front seat, and was extending his hand to help the women down from the cab next to the curb. Maybe Dean _did_ need to take ‘gentleman’ lessons from him, after all.

Jo took his hand, and stepped out, looking him from head to toe, thoughtfully. After a moment, she responded, “He _might_ be able to lift ya. Hasn’t worked out ina while, so g’luck.”

Meg threw her head back and cackled, as the remaining three girls giggled hysterically, and one by one, were helped out of the car by Cas' waiting hand. He just _winked_ at Dean, and wished each of them, individually, a safe night. Dean was nearly tempted to take Cas’ hand too and follow the chicks into the damn hotel, because he was about to die of embarrassment at anytime. But, he didn’t get the chance. Cas hopped back into the cab, blocking his escape route and taking Meg’s seat, while directing the cab driver to _his_ hotel.

Dean snorted, a bit defensively, “So, you want a piggy?”

“I think I can walk on my own, but thank you for offering,” he reached out, and looped his fingers through Dean’s. “I can think of more enjoyable ways to spend the night. Although,” he leaned in just enough that Dean could feel the man’s body heat radiating on his cheek, “you turn the most beautiful shade of red when you’re embarrassed.”

“Ugh,” Dean smacked the back of his skull against the headrest, “Those girls are vicious!”

“Pack animals, preying on the weak,” Castiel mused, a smirk playing over his features, “But they’re quite fond of you, so I wouldn’t be too upset.”

“Strange idea of ‘fond,’ Cas. Don’t tell me that's how _you’re_ fond of me. I dunno if I can take much more harassment tonight.”

He shook his head, his eyes closing for just a moment, “I’m fond of you in a very,” his gaze locked with Dean’s while he unhooked their fingers, “very,” and then trailed them over the fabric covering his crotch, “different way.” His hands repeated his motions, this time raking his nails along the path, but still _teasing_. “At least, I _hope_ so.”

“Mr. Krushnic?” The cab driver asked, for what may have been the _second_ , or _millionth_ time, Dean couldn’t have been sure.

He was too busy staring, and zoning out on Castiel’s mouth and all the things he hoped slash wanted it to do tonight. But the other man was the first one to pull away, as he reached into his wallet to pull out the cab fare. Even drunk-ass  _Dean_ knew, as he glanced at the wad of money, that he tipped obscenely well. Damn, did he end up with some Russian mob boss or something? But at this point… _anything_ about Cas, he’d find sexy. Even ( _especially_ ) if he threw people in the ocean so the cops couldn’t find the bodies.

For the first time, a truly excited grin lit up on Castiel’s face, as he snagged Dean’s wrist and tugged him out of the car. Why did this dude make Dean feel like he was sneaking someone into someone’s house in high school? It was a thrill, like something _new_ , even though it was far from it. This random asshole gave him butterflies, and he had _no good explanation_ as to why. Maybe it was because he was gorgeous? Maybe because he kissed him like their mouths were made for each other? Or (god was the wine that somehow slithered its way down his esophagus that night making him sappy) was it the way he looked at him like he was _special_?

_Where did that come from?_

Wine. Definitely wine. Becky liked that shit, maybe she had-

The concierge nodded at Castiel and Dean as they ripped through the lobby, which was thankfully empty, minus the hotel employees, and headed to the elevator. Cas barely managed to punch the button for the top floor, before he had grabbed the hand rails and boxed Dean against the faintly mirrored wall. He was _on_ him again with ferocity, all clashing teeth and needy moans. Dean’s hands had a mind of their own and instantly snaked around to grab handful of Castiel’s ass to get him closer.

And _fuck_ , was that a _nice ass_.

Not to mention, the bulge currently rutting against him mercilessly was pretty nice too. Shit. He was trying so hard not to cum in his pants like a goddamn teenager, but the way Cas was gripping the rails, using it as leverage to grind with even _more friction_ against Dean was _unfair_. He wouldn’t be held accountable for his actions-

Thank god, the elevator dinged. Literally - saved by the bell.

Cas fumbled in his pocket, to grab his key-card, walking ahead of Dean and taking deep breaths. Apparently, he was on the exact same level, and trying to gather himself too. A self-satisfied smirk appeared on Dean’s face as he nodded, confirming that he _still had it_. Too caught up in congratulating himself, it took him a second to realize Cas had stopped in front of a door, key-card in hand, _blatantly_ checking him out. Which made Dean falter in his steps. So he did the only thing he knew how to do in these situations.

“See something you like?” And he winked.

Cas looked up at him with dark eyes and bit his lip, “I see many things. But I can’t help but imagine what those perfect bow legs will feel like wrapped around me in about five minutes.”

All right, _that_ made him _blush_. “Call ‘em like you see ‘em, huh, Cas?”

“My filter isn’t up to snuff on the best days, let alone when I’m intoxicated,” he finally stuck the card in the lock. “Or _impatient_.”

Annnnd that was his cue.

Castiel flicked the lights on, and immediately flung off his suit jacket. Which, all by itself made Dean’s erection twitch, because he seemed like the kind of guy to fold it up neatly, not wad it and throw it in a corner. _That’s_ how bad he wanted him. Well, might as well take it all the way. Press boundaries. Liquid courage, and all that. Dean was feeling feisty.

“Want you so bad, Cas,” Dean finally caught him off guard, and cornered him against the wall in the entry way. “Like, yesterday.” And _went for it_.

He untucked the pristine, white button up from the bottom of his trousers, and _jerked_ it. _All the way up_. Sending buttons flying everywhere. His original plan was to shut up his _inevitable_ bitching and complaining by kissing the living fuck out of him. But then he got distracted. By the perfect expanse of tanned, muscled skin, jutting hipbones and _statuesque_  sex lines.

“See something you like?” Cas repeated his comment from earlier with a crooked grin, and took the dumb-struck expression on Dean’s face to his advantage and paid him back.

By ripping _his shirt_.

Dean _should_ have seen that coming. But, dammit, he actually _liked this shirt!_

With a dark glare, he aggressively yanked the buttons of Cas’ pants, when the man leaned forward, and purred into his ear, “You look upset, Dean,” while he sucked marks into his skin.

He shivered at the contact, and couldn't help but moan, “whatever,” as one hand slipped below the fabric of both Cas’ pants and boxers, the other griped the front and he slowly slid them down.  _Dean_ joined them - and crouched on the floor while the clothing pooled around his ankles. He grinned up at Cas, who had to brace his palms against the wall to take in the sight before him.

All right, so Dean had to admit, he wasn’t quite as experienced with guys, as he was girls, so now, at eye level, Castiel’s cock was _more_ than a little intimidating. But that was completely overshadowed by the exciting and desperate need to have it down his throat _right the fuck now._ Not to mention the way Cas was watching him, completely enthralled and looking like he was going to lose it? _More_ than enough fuel for the fire. He grabbed it by the base, feeling the heavy weight in his grip before swirling his tongue around the thick head.

The delicious noises from above were spurring him on, he continued lapping along the length, coating his entire dick with wetness before returning to the tip. Dean sucked, teasingly at first, just a _little_ into his mouth, noticing the slight buck of Cas’ hips. He was doing _so_ good trying to hold back. He thought he’d reward him. But not _right_ away. He liked this game.

Little by little, with each bob of his head, he took a little more into his mouth, the pre-slicked cock gliding smoothly against his wet lips. A harsh grasp, punctuated by a fist slamming against the wall hit, when Dean finally took him down his throat enough, he had to move his hand from the base to Cas' thighs instead . His body was relaxed enough from the alcohol he didn’t even gag. More than anything, Dean wanted to _please him._ Cas double over, moaning, and threading his fingers through Dean’s hair to gain purchase of _something_ as Dean continued to deep throat his cock. His eyes were watering, by the time Cas couldn’t control himself any longer and began thrusting into his mouth.

“Dean - _fuck_ , I … Bed. _Now_.” He straight-up _pulled_ Dean’s hair to get him away, he was so close to riding that edge, because he meant it when he said he needed him _now_.

Castiel manhandled him to stand, and when Dean went to flick the light switch to ‘off’ Cas snatched his wrist away and continued to tug him into the room. “No.” He ordered. “I need to see you when I take you apart.”

Yeah. That made Dean gulp.

One minute, he was in the entryway. The next, he was shoved, face down, on a bed that may have surpassed Jo’s suite in terms of luxury. If that was even _possible_. And when Dean caught a glimpse of the room, _shit_ , it really had. _How_ did he end up in this situation, again?

But then, his thoughts short-circuited. Cas had him by the back of the neck, pushing him into the mattress, while the other hand gripped at his hip and he felt a hot breath on his back. Then a fucking _tongue_. It was _just_ as hot, as the man behind him licked a strip from the cleft of his ass, dragged it slowly over his hole, and lapped at his balls. A shiver ran down Dean’s spine, and he _barely_ rose off the bed, just to get smashed with a face-full of pillow again.

A gruff voice snapped, “Stay,” and Dean could only nod.

The hand on his throat left, as well as the hand on his hips. So this was a challenge, huh? Dean could _do_ a challenge. Soon, both hands were cupping his ass cheeks, and spreading them wide open. Dean would have been embarrassed as all hell, being vulnerable like that, if Cas’ tongue wasn’t circling his opening and making him writhe like a fucking whore. Dean desperately grabbed at the sheets, but kept his head down, and his ass up. That was when Cas’ tongue breached his hole and started licking inside him.

He whimpered - because _this_? _This_ was _new_. He’d never let _anyone_ eat him out before, would have slapped them away if they’d even tried - but Cas? He’d let Cas do _anything_. Anything he wanted.

Dean could feel the wetness of saliva between his legs, dripping enough to reach his balls, and when the heat left, he groaned at the loss of contact. Until he heard a different noise. Because, yep. That was definitely Cas sucking his fingers. His tongue was back, but so was a thumb. Shit, why couldn’t he have started with something a little smaller? But, apparently, Cas had done a damn good job of relaxing him, because as the thumb gentle circled his opening, his tongue was able to coax him enough into giving in. And, with little resistance, the thumb pushed _in_ too. It started, slowly at first, thrusting in and out of him. Dean never thought he’d say it, this was usually a means to an end, but he wanted _more of this_ , pronto.

Foreplay was never really his thing, he wanted to get to the main event. But Cas, his tongue, and this? Heaven… and he-

Another thumb pushed inside him.

Okay, that was a little rougher than the first.

He winced, and tried not to make a noise, but his _lack_ of noise was what prompted Cas to ask, “Is that all right?”

“Y-yeah.”

“Just relax, Dean,” it was soft. And soothing.

Dean liked it. A lot. Soon, after he did relax, he also liked the way both thumbs were massaging his rim, and how Cas’ tongue was fucking him even deeper. He couldn’t stop his body from thrusting backwards into that man's mouth, trying to urge him along.

Cas finally shifted, and exchanged his thumbs for three fingers, while his other hand looped around Dean’s middle and began stroking his cock. The fingers changed _everything_ , when they nailed his prostate after a few pumps. He couldn’t lay prone on the bed any longer, he snapped his head around to Cas and demanded, “God, just fuck me already,” because by now… it was torture. Sweet, sweet torture. But _torture_ , none the less.

The bastard didn’t give in right away. No, he decided to shift his own cock between Dean’s thighs and thrust in time with his digits and fist, like he was _going_ to fuck him, but wouldn’t _quite_ yet. So Dean took to whining. And _begging_. Which earned him a biting bruise to his shoulder blade, and Cas nailing his prostate again and again. He was _close_ , so close, _again_. _This man was going to kill him._

“Dean,” he mumbled into his ear. “I… don’t have anything.”

This could have been a fucking _disaster_ , but awkwardly enough, Dean had been wishfully thinking about getting with one of the bridesmaids. Oh, how the tables had turned. He didn’t regret it for a second.

“My pants-” he grunted out, his voice sounded breathless and strained in his own ears. “Got a condom in my pants.”

In a flash, Cas was gone from the bed, and gone from _Dean_. He could have sobbed, being alone, but settled instead for ungracefully falling over on the bed, because he couldn’t support his weight anymore. On his side, he could watch the way Cas’ muscles flexed and stretched, while digging through his pockets. And that stare at that ass. Especially naked... Dean really _was_ starting to get obsessed with it. As soon as Cas found it, he moved like lighting, over top of Dean, pinning his arms to the mattress.

His grin was predatory as he asked, “Think you’re ready?”

Dean would have rolled his eyes, if he didn’t think it Cas would torment him more than he already had. Which would be the end of him. And Jo still needed him in her wedding, so he refrained. Instead, he spread his legs, and wrapped one around Cas to pull him in. The man’s breath caught in his throat, and the sheer _need_ on his face made Dean agree they _definitely_ made a good choice in leaving the lights on. Castiel ducked his head forward, and proceeded to kiss Dean as breathless as _he_ was. He nipped at his bottom lip, and tugged, before sucking at his neck and taking for few more fleeting seconds to worship his body.

Soon, he was ripping the condom open, and rolling it down his leaking cock, a bit shaky, which made Dean’s head swell a little bit. Apparently, Cas hadn't gone unaffected, and wasn't as calm and cool as he pretended to be. Which was gratifying. But then, Cas looked kind of _apologetic_  towards him, and Dean _knew_ why. Yeah, Dean had a _condom_ , but once again, he was planning on hooking up with a _chick_ that night, so of course they didn’t have _lube_. Sure, the condom was lubricated, but that wasn’t exactly ideal. Dean was pretty damn wet from Cas’ mouth, though, so it wasn’t _impossible_ , or anything.

Cas still leaned down and kissed him on the lips, in a strangely _tender_ kind of way, “I’ll go slow, tell me if it hurts.”

Dean’s _heart_ hurt. Should he tell him that? Or would that be awkward? The way Cas was treating him, like he really was something special, like he mattered? He could really fall for this guy. Annnnnd the wine struck again…

So he just nodded, dumbly.

Castiel lined up, and started to push in as slowly as promised. He watched Dean’s face, as he sunk inside him more, his eyes never leaving, looking for some telltale signs of discomfort. Which made it even _more_ of a difficulty for Dean not to look uncomfortable when a huge dick was being shoved inside his asshole. He didn’t want him to stop, even if the stretch _did_ burn, but he wasn’t going to show it. He tried to bite his lip, and just nod for him to continue, because once it was finally fuckin'  _in_ and he got _used_ to it, it’d be fine. He had to keep telling himself that because, _okay_ , this kinda sucked. It sucked even more when Cas made a move like he was going to pull away.

“No,” Dean hastily cupped Cas’ face with both hands and brought their lips together again. He kissed him hard, trying to _show_ him it was fine, he didn’t need to stop, because this was what he was craving. A hand covered one of Dean’s and he melted into the kiss eagerly, and the distraction was all he needed to be completely sheathed in the heat of Dean’s body.

They were still, aside from the gentle kisses for a handful of moments, before Dean nodded, accidentally bumping their foreheads together. Cas experimented with rolling his hips, not quite pulling out yet, giving Dean any chance he needed to say it was too much. Dean bucked into the touch and moaned out loud. Yep, that felt _great_. He was _more_ than ready.

Cas didn’t hold his hips down and fuck into him like a means to an end. He sucked his neck, and nipped his earlobe, always returning to his mouth as he withdrew and thrust back into him. He started off slow, and built up a rhythm, adjusting Dean’s hips until the man shouted out - it was the tell-tale sign he’d found his sweet-spot again. Then he didn’t hold back.

He pounded into him, pulling away only to let him breath and watch his face, as Dean came unraveled. His arms grabbed at Cas’ back, and his nails sunk into the expanse as he felt himself getting close. Fuck, he didn’t even need to touch himself, Cas didn’t even need to touch him, he was going to cum on his cock, and his cock alone. And that was one of the hottest things he could think of. So many earth-shattering firsts were happening this night (morning?), and he didn’t even realize he could _make_ the noises coming from his throat until Cas went all out.

There were no words - no screams of ‘faster, deeper,’ - just echoed moans and noises, because that’s all there needed to be. In these moments, it was just _them_. They fit together, their bodies felt like they _knew_ each other, everything made _sense_ and it was _real_. God, Dean had never felt anything like this, with anyone else. It was a connection, it felt... different, more meaningful and so alluring…

They were _definitely_ waking the neighbors.

Dean was arching, digging his heels roughly into Cas and this time he knew he was going to blow his load. Third time’s a charm. Right as he fell off that ledge, Cas sucked a desperate bruise into his neck, and he was _gone_.

Cas was gone too.

Dean might as well have blacked out, because the next thing he knew, the man had pulled out of his body, the condom was gone, and he had somehow wound up laying on Castiel's chest. He was still catching his breath, when Cas wiped down their stomachs with the edge of the comforter and pressed a kiss onto the sweating mess of Dean’s forehead. When he looked up, he was greeted with a goofy smile, and another tender kiss on the lips. And fuck, if Dean wasn’t down for some cuddling.

Except, before the afterglow have even worn off, Cas was shifting around, and it was _seriously_ killing Dean’s buzz.

He poked the man in the side, as Cas grabbed his phone. And then, with a heavy sigh, the man stated, “I’m sorry to cut this short but-”

“ _Really_?” Buzz killed. Murdered. Dead. “Dude. We _just_ had sex, like, fifteen seconds ago, and you’re already kicking me out?”

“I’m not meaning to, I have a plane to catch, I’m sorry, Dean-”

“Stop. Right there.” If looks could kill, Cas would be blow to pieces right then and there. “Couldn’t even wait until I dipped out before check out? Even for fuckin’ _one night stands_ , it’s _protocol_ to at least fall asleep for an _hour_. Nice excuse, there,” Dean shoved off him, and ignored the vertigo in his head to stand up from the bed.

Cas looked like he wanted to say something, but Dean was quickly crossing the room to pick up what was left of his clothes. He yanked his pants on, not bothering to turn back around and face the man. _Being ordered to leave_? Like a fucking _street walker_? If that wasn’t a slap in the face, he didn’t know what _was_. And fuck, if for two seconds, Cas didn’t make him feel special. Now that was ruined, his fantasy shattered, and he felt like the biggest _idiot_ in the world.

He nearly tore the zipper off his pants as he pulled them on, and he heard Cas say, “I told you, I was here for business and-”

“Then you should have ordered a _hooker_! You have enough money for it, asshole!” Dean shouted, his anger boiling over, because he was _not_ the guy who got played.

He _did_ the playing, and his ego was hurt.

And his heart kind of hurt too.

And his ass. His ass hurt a lot, actually.

“I didn’t want a hooker, if you’ll just let me-”

“Fuck you, Cas!” Dean pulled on his shirt and went to work on the buttons but…

It didn’t _have_ any buttons.

“Goddamit!” He raved, and grabbed the blazer.

He was angry drunk now, and it was growing by the second. Especially when Cas had the nerve to say, “What can I do to make it up to you?”

Dean clenched his fists and _almost_ charged into the room to shout some more, until something caught his eye. The minibar. He wanted a drink _now_. He wanted to drink himself into oblivion, after this bullshit, and sweating all the alcohol out. So he _went for it_. He threw the door open, and grabbed an single-shot of whiskey and tossed it back. He threw the bottle across the hotel room, and whipped around, as if _daring_ Castiel to say something.

The man just stared at him, apologetically, from the bed. _He_ looked hurt. And he had _no reason,_ in Dean’s mind, to look hurt. Which fueled the fire, and Dean thought _fuck it_.

“I’ll take my tip, fuck-face!” He reached into the small refrigerator and acted on drunken impulse alone.

And began stuffing bottle after tiny bottle into his jacket. Then his pants. Then _down his pants_ , which was a _terrible_ idea, because those bottles were _fucking cold goddamnit_ , but it was to make a _point!_  He slammed the fridge shut with a dramatic kick, and threw Castiel a middle finger.

“Have a nice life!”

He jetted out the doorway, even though he heard the rough shouts of his name, but didn’t care.

Dean ran.

_Straight up ran._

With his tail between his legs, full speed, and didn’t even bother with the elevator. He took the stairs, two at a time, and in retrospect was very proud of himself - he didn’t tumble down to his death. Dean’s thoughts, and the journey to the street was a blur of frenzy, resentment, and berating himself for being so fuckin’ stupid. In the ‘throes of passion,’ he was tinkering with the idea of love at first sight. And if that was the case, was this heartbreak at first parting? He flew down the street, and was lucky enough to see a cab parked outside the hotel.

It was _daylight_ now. It burned his eyes, as he stumbled, and face-planted into the taxi.

“Sir?” The man asked cautiously.

“Hotel,” Dean grumbled from the leather seat cushion. “Back. Hotel.”

“Which hotel?” The cabbie started the engine, as Dean began to sit up.

As he did, he caught movement out of the corner of his eye, and saw Castiel, with his goddamn matching _ripped shirt_ , out on the street looking around desperately. Even from here... he could see desperation in those freakin' too-blue eyes, and it carved a new jolt of pain through him all over again. Dean ducked his head back down, hoping Cas didn’t catch sight of him and ordered to the man, “ _Drive_ , dude! Just drive, _now_!”

He raised an eyebrow, but flipped on his turn signal and then pulled out into traffic.

Dean finally popped his head out, and made eye contact with Cas, who looked _just_ as broken as he _felt_. Serves the fucker right.

Taking in a few calming breaths, and trying to keep his own shit together, he tried to think. And then realized... His drunk brain _wasn’t_ cooperating with him, and he had no idea what the name of the hotel even was. “ _Motherfuck_. I’ve lost brain cells.”

“Can you describe it?” The man was strangely patient, probably used to dealing with drunk idiots all the time, and Dean raked his brain.

“Uhh... It’s close to the 451 Bar... There’s double doors... A carpet?”

“A lot of hotels are like that,” the man scoffed, “But we’ll head in the direction of the bar, and see if anythin' jumps out at you.”

Dean nodded, and looked at his feet. Godammit. He wanted to cry. _Why_ did he want to _cry_? Was it that last shot of whiskey that finally did him in? He was miserable, he’d hit a low, and that final slap in the face made him want to jump into oncoming traffic. He tried to school his features, and clear his throat, looking out the window.

“Rough night?” The driver sounded genuinely sympathetic.

“Y-Yeah.”

“I have a son around your age,” he mused, glancing at Dean’s reflection in the rear view mirror, “He had that same look on his face when his damn fiancée left ‘em.”

“Nah, nothing like that,” putting into perspective like that, Dean felt _stupid_. It was just a one night stand, right? _Why_ was he getting so tore up about it?

“Well, if it hurt you, it hurt you. Was it that boy back there? Looked like he went a couple rounds with a lawn mower?”

Dean blushed about how candidly, and without judgment the man talked about the fact _he had just been fucked by another man_. “Yeah. I was the lawn mower.”

“He looked pretty hurt too, ya know.”

“It’s whatever.”

There was a silence in the cab, before the driver spoke up again, “All right. There’s the bar. Now, the hotels are comin’ up on your right. Any of ‘em look familiar?”

Dean whipped his head around so quick he almost collided with the window. His depth perception was _really_ off. As they passed, he kept staring, thinking nope. Nope. Nope. But then, one with familiar brick lining caught his attention and he quickly announced, “Found it!”

The man chuckled, and pulled in the circle drive, “That was relatively painless.”

“Yeah, in comparison to my night, and how I’ll feel in the morning,” Dean mused, and dug through his pockets. “Dude, seriously. Thank you for putting up with my drunk ass.”

“No problem,” he smiled. “This one’s on me. Like I said, I’ve seen that face before. You have a good day, ya hear?”

Dean blinked owlishly and asked in a quiet voice, “You sure?”

“Yeah, you need some good karma to come your way. Now get out before I change my mind.”

“Thank you…?”

“Rufus.”

“Thank you, Rufus. I’m Dean.”

“All right, Dean. No more lawn mowing people. Get your ass to bed.”

“Yes sir!”

He hopped out, and waved at the man, before pulling out his phone. He quickly called Jo’s phone as he walked in the hotel, to get her to let him in.

It went right to voicemail.

As did Charlie’s.

And Jessica’s.

And _fuck_ , he didn’t have anyone else’s number.

He hoped he remembered the hotel number correctly, his steps were heavy and he was still drunk as a skunk when he found himself where he hoped was ‘home’ for the night. He knocked lightly, but there was no answer. He kept knocking, but no one came. His _legs_ were tired. _He_ was tired. And he wanted to curl up in a ball and hibernate. Forever, possibly.

He leaned against the doorway, and let himself sink to the ground. Would he get yelled at if he slept out here? He had no idea how long he could keep his eyes open… but none of these drunk chicks were answering, all passed out cold, or something and he was without a way in. He tried knocking a few more times, but to no avail. Fuck his life.

\-------------

Dean didn’t know how long he was sitting hunched outside the doorway to the room, but he did know his bladder was due to explode at any second along with his fucking ego. Nope. That was over and done with, _already_ splattered, metaphorically, all over the walls. But, _finally_ , he heard the door creak open, and the _last_ person he wanted to see, let alone _explain_ himself to, sneaked out the door.

Fuckin’ _Gabriel_.

He crouched down across from him with the brightest grin on his face, considering it was ass o’clock in the morning, and the man should have been hungover as all hell. But, nope. He was squatting across from him, looking like a ray of fucking sunshine, and that was _not_ what Dean needed right now when he was still drunk, and starting to feel a throbbing headache pounding against his skull. And he still really, really, really needed to piss.

“Soooo,” Gabriel started, way too cheerfully, “You headed home on an airplane?”

“What?!” Dean demanded, his voice hoarse and way too loud for his own ear. “The _hell_ you talking about?”

“Looks like you’ve got about half of the mile-high club accomplished,” Gabriel reached across the small space between them to smack at the pockets of Dean’s blazer, and set off the tell-tale slosh of booze in his pockets.

Dean’s jaw fell open, “How... What… _How_ did you-?!”

“While I’d love to razzle dazzle you with psychic abilities, when I heard your knocking, and I looked to see what time it was, I _also_ saw a text on my phone,” he wiggled his eyebrows, and Dean did _not_ like where this was going. “ _Apparently_ , you got your panties in a twist, after you pulled them _back on_ and made quite the dramatic exit on my bro.”

“Your _brother_?!” Dean yelped, and nearly tumbled over on the floor.

“Yep. _You’re_ the drunk asshole, _not_ him,” Gabe stabbed a finger into Dean’s chest, where one of the many bruises under his shirt was. “He really _is_ here on business and needed to head out. I wanted to meet up with him last night, or this morning, I don't know anymore... at that piano bar but when I saw _you two_ were hitting it off I took a step back to let ya have at it. Soo anyways! He wanted your fuckin’ number and to see you again, but you ditched him in a tizzy before he could _do_ anything. Nice work tappin' that, by the way. He’s usually kind of a prude.”

“The hell he is,” Dean _still_ couldn’t believe his ears, and his face reflected it. But only _one thing_ was sticking, in this whole entire _apparently misunderstanding_. He had sent Gabriel a message. Which _meant_ something. “He... Wants to see me again.”

“Idiot. Text him and see for yourself.” Gabriel rolled his eyes, and grabbed Dean’s phone out of his hand. “Little bastard’s already in love with you. You must be an awesome lay, because I don’t see what the fuss is all about.”

Dean would have punched him. He really would have. If he didn’t want to kiss him. What the fuck was going on.

“There. Done!” Gabriel handed him his phone back, then stood up, extending his hand down to Dean, “You gonna stay in the hallway for the rest of the time?”

He shook his head dumbly, and accepted the hand.

“Good. We still got a few more hours til check out. Just keep quiet, and find a nice space on the floor. All the amazons are knocked out cold. Looks like we did our job last night,” he winked, and silently pulled the door open.

Dean wordless rushed to the bathroom to relieve himself. Once he was finished, and washed his hands, he looked at the contact Gabriel added to his phone and felt his heart in his throat. It was listed under ’Future Baby Daddy.’ Fuckin’ Gabe.

Using the last bit of liquid courage he had left in his body, he quickly typed a message.

_Have a good flight._

It was simple. To the point. It told Cas that he believed him, and kind of (as much as _Dean Winchester_ was capable of) apologized.

He took a deep breath and slowly started unloading all the loot he had stashed in his pockets on to the bathroom counter. As he lined up the bottles, he felt half ashamed, and half impressed with how much he had managed to tuck away in such a drunken fit. Okay, maybe he was more impressed than anything. He shook his head, and looked at his reflection in the mirror. He looked well and truly fucked. About one hundred _different ways_ of fucked, too. Hot mess-fucked, still drunk as fuck, and _well-fucked._

Most _definitely_ well-fucked.

His phone buzzed, and he had to mentally convince his hands to work as he tapped through his touch-screen to pull up the message.

_I assume and hope this is Dean. Thank you. I’ll call you when I land._

Dean typed back quickly:

_As long as it’s after 1pm_

He didn’t even get the chance to put his phone down, before another text appeared on the screen.

_Very well. I hope to see you soon. You owe me a drink_

Instantly followed by-

_Or ten_

After meticulously counting out the bottles, and with the dopiest grin ever on his face, Dean responded one more time.

_You’re close. 14._

Castiel didn’t say anything for a second, and Dean assumed he packing or on the way to the airport. Or maybe he has just thought about the situation again and realized what a fucking _child_ Dean had been and how he was just wasting his time. Feeling slightly defeated, Dean reached out to grab the handle to the door, _more than ready_ to pass out the moment found a stretch of unoccupied floor.

But then, his phone vibrated.

_I’ll be happy with one. Consider the rest my treat._

He laughed out loud. All right, so maybe, in addition to all those other kinds of fucked he looked... he was kind of _head-over-heels_ fucked, too. Oh well.


	3. Dean Winchester +1

**Summary for the Chapter:**

> _All right. So, Dean considered himself a man of good ideas. Great ideas, for the most part. However, on the other hand, he had just as many terrible ideas. He hadn’t decided which of these it was._
> 
> _Their entire situation was unorthodox._
> 
> _Obviously._
> 
> _How the hell did he end up asking a one night stand to be his +1 to his best friend’s wedding? And why the hell did said one night stand agree? Castiel was a mystery wrapped in one hell of an attractive package. Scratch that, he was sexy as fuck. And he had an attractive package? This was all besides the point!_
> 
> _All he knew, is that he really, really, really wanted to see Cas again._

**Notes for the Chapter:**

> Instead of creating a new work, I decided to add on to "Buy Me A Drink First." The plot of the 'sequel' is in this chapter's summary.
> 
> So here ya go! Welcome to "Dean Winchester +1" <3
> 
> AND HAPPY NEW YEAR! xoxo

All right. So, Dean considered himself a man of good ideas. Great ideas, for the most part. However, on the other hand, he had just as many _terrible_ ideas. He hadn’t decided which of these it was. It was one of those mind over matter or heart over… _okay_. He was being stupid. Sure, they’d been talking. They had a good thing going, as far as these long-distant, kinda-keeping-in-touch-but-we-both-have-hella-busy-lives went. As he re-read the text conversation he was deliberating in his mind just what the fuck he had gotten himself into.

_Sent_  
 _So, remember Jo?_

_Cas_  
 _How could I forget. How soon until the wedding?_

_Sent_  
 _Sooo about that. Got any plans April 13th?_

_Cas_  
 _Not that I’m aware of. Why?_

_Sent_  
 _Wanna hang out with me and Jo again?_

_Cas_  
 _Are you asking me to be your wedding date_

_Sent_  
 _Pretty sure that part was obvious_

_Cas_  
 _I’m agreeable_

_Sent_  
 _Sounds great! So awkward question. Where do you even live dude. You know this is in Kansas right_

_Cas_  
 _Yes, I can make it to Kansas. I believe Gabriel was already going, I’ll work out travel arrangements with him._

  
Dean knew the other man was deflecting, he didn’t even answer the question about _where the hell he lived_ , which should have raised red flags, but it... didn’t? Their entire situation was _unorthodox_.

Obviously.

How the _hell_ did he end up asking a one night stand, to be his +1 to his best friend’s wedding? And why the hell did said one night stand _agree_? Castiel was a mystery wrapped in one hell of an attractive package. Scratch that, he was sexy as fuck. And he had an attractive package? This was all besides the point!

All he knew, is that he really, really, really wanted to see Cas again.

\-------

_Sent_  
 _Hey_

_Jo_  
 _What’s up hoe_

_Sent_  
 _So I think I’ll be using that +1_

_Jo_  
 _STFU who are you bringing?!_

_Sent_  
 _Cas is in_

_Jo_  
 _In you, you mean???_

_Sent_  
 _I hate you so much_

_Jo_  
 _You love me! Can’t wait to see that handsome devil dressed up. Charlie and I think he’s dreamy_

_Sent_  
 _Paws off he’s mine_

_Jo_  
 _Wouldn’t want your sloppy seconds! Besides I’ve got a man of my own if you didn’t remember_

_Sent_  
 _Yeah yeah just wanted to let you know you ass_

_Jo_  
 _Oh the ass jokes I could make!!_

_Sent_  
 _This conversation is over_

_Jo_  
 _Just don’t find another sexy Russian at Benny’s bachelor party Cas might be jealous_

_Sent_  
 _Wouldn’t dream of it_

\-------

Dean didn’t even have the excuse of being drunk when he invited Castiel out to the wedding. However, he _did_ have alcohol to blame at Benny’s bachelor party. And that’s when drunk dials and shit hit the fan.

But it wasn’t really his fault, you know? Ever since he had to play bodyguard at Jo’s bachelorette party, the nights kind of ran together, but the main thing was - Cas wasn’t here this time.

After about one too many bourbons, beers and thankfully many a man-drinks (none of that slipper nipple, sex on the beach, white gummy bear shit he had to endure last time), Dean still kept seeing flashes of dark hair and blue eyes out of the corner of his vision. Even the strippers resembled Cas.

You know. Minus the tits. And vagina.

Chick assets - which Dean didn’t really miss. Dean was kind of obsessed with Cas’ cock - and when he had enough time in the shower, he’d finger himself trying to remember how it stretched him full…

“Dean?” An finger poked him in the side, “What’s with the heart-eyes?”

Heart eyes, _really_? He was fucking _lucky_ he didn’t have a _goddamn boner_...

Before he even registered _who_ it was, he retorted with, “No, I don’t!” Until he realized it was his brother… and _then_ he was fucked.

Sam could read him like a book - knew all his tells, and could obviously notice right away where the defensiveness was coming from. And it ain’t coming from anywhere _good_. As if the shit-eating grin on his face didn’t say enough to begin with. Yep. Dean was fucked. So he gulped. Especially when Sam reached out, patted him on the back twice and then bumped their shoulders together.

“You’re either in love with a stripper, which I hope you’re not - since we didn’t exactly get the A Team ‘cause it‘s Wednesday night. Or-”

“Happy hump day!” Garth cheered in the background, hearing the word ‘Wednesday,’ and then tripped over a bar stool.

There may or may not have been shattering glass and a shrill scream from their lightweight friend. Both Winchester’s ignored him, and shook their head. This was nothing new.

“Or-”

“Or, _nothing_!” Dean groaned, “Just lay off, bitch, don’t kill my buzz!”

“Dean’s gotta cruuuush,” Sam raised two fingers to the bartender, who quickly brought over two beers, “Tell me about her. Him. What are you into, these days?”

“People aren’t a hobby, dude! You can‘t just say ‘ _what’re you into these days,_ ’” Dean groaned, and snatched the neck of the bottle from the bartender and took a swig. “But, uh, it’s a him?”

“This the beau you’re bringin’ to the wedding?” Benny pulled Dean into a head lock and shook him, while Sam’s eyes lit up.

Dean barely managed to whimper out, “Jo told you?!”

“Duh. Gotta ‘prove of the guest list, brother.” He grinned widely, and couldn‘t help but giggle (and Benny very, _very_ rarely giggled) “Although, I was confused as to why you weren’t just down for a plus one, and Jo’d actually had ‘Dean’s Future Baby Daddy’ with a heart next to it by yer name. But when she told me the story, I gotta say… that’s a new one. Even for _you_.”

“Fuckin’ Gabriel! His name is _Cas_ , not whatever bullshit Gabe comes up with. I’m done with the crappy nicknames.”

“What?! How long have you guys been dating?!” Sam demanded, getting that stupid giddy puppy dog face he got, like it was _Dean’s_ wedding, or some shit. “Why haven’t I met him?! I can’t believe you’ve kept him from me for so long, Dean! I can’t wait!”

Benny and Dean exchanged awkward looks, and _dared_ the other person to say something.

Because, _really_?

Benny was right - this _was_ a new one.

“Well, we’ve only really ‘ _hung out_ ’ once, but we really hit it off, and we’ve been through a good amount of shit and… uh… _problem solving_ and we text a lot, er, once in a while, so, I mean, it’s _like_ we’ve been dating…” Dean’s voice was as slow and steady as his drunk mind would allow.

Until Benny couldn’t take the bullshit anymore, and corrected: “Dean fucked some dude at Jo’s _bachelorette party_ , threwa _temper tantrum_ and blew something out of proportion and said dude _turned out_ to be one’a Jo’s _bridesmaid’s brothers_. And Dean’s in _love_ with him.”

“Am not!” But then Dean turned pale, “Holy fuck, I didn’t even think that he was _Anna’s_ brother too, _hell no_ , I _have_ to take this back, I’m gonna make an ass out of myself at this wedding with _half his fuckin’ family_ there all because I just wanted to see him again and-”

“Deep breaths-” Sam was almost speechless at the sheer _ridiculousness_ of it all, but the fact that Dean was about to hyperventilate brought him to hand the beer over, in an attempt to calm him down. “If _Jo_ said it was cool, it’s cool - right?”

“I need some air…” Dean grabbed the beer, and charged before anyone could say anything else.

He didn’t think as he stumbled through the door, and nearly fought the bouncer to bring his beer outside, but gave up and set it on the table before exiting. The days were warming up, and he swung himself around in the night air before something inside him told him he _needed_ to talk to Cas. _Now_. Who the hell cared it was a Wednesday night, at 1am? He could just say hi, chat for a sec and go back to sleep _right_? Duh.

Dean fumbled with the passcode on his phone so many times he nearly locked himself out (why didn't he just have one of those fingerprint reader thingys already?!). He puffed up in annoyance as it counted down failed attempts and told him he had _one_ more try left. By some _miracle of God_ , he did it. He took no time scrolling down to Cas’ name (which he had quickly changed from Future Baby Daddy - once he was sober again and back home in Lawrence.)

The man’s throat was dry when he went to voicemail.

Maybe Cas was in the shower?

So, _obviously_ , because he was drunk, he called again.

Voicemail.

And then, third time’s a charm!

A gruff voice answered the phone, foggy with sleep and he could barely make out a “… Yes…?”

“Hiya, Cas!”

“Hello, Dean. I can only assume you’re intoxicated right now.”

Dean blushed, but was thrilled (freakin’ thrilled) to hear the other man’s voice, no matter how grumpy he sounded, “Yeah dude, _bachelor_ party. No responsibilities, no chicks to watch over, beer, strippers, the whole nine! Buuuut there’s no you. And _that_ kind of sucks.”

The chuckle on the other end of the phone sent warmth from the tips of his toes right up through the top of his head. God, he _loved_ that sound.

“I’m sure the lovely ladies of the club will keep you company in my absence.”

“Don’t want them. Want you.”

Dean could hear the shifting of fabric and guessed that, yeah, Cas was probably _definitely_ in bed and he had woken him up. Too bad he wasn’t there with him. They still didn’t get the chance to cuddle and any excuse to wrap around Castiel’s body was-

“I’m flattered. Make sure you drink plenty of water tonight, Dean,” he paused for a second. “I’m happy you’ve been thinking about me.”

“Thinkin’ about you a lot. Can’t wait to see you. You should come early-” Dean suddenly had the _best_ idea _ever_ , “Or stay longer! I dunno, just wanna spend more time with you. Or something. _Fuck_ , I’m being a girl. Maybe we should just pretend this never happened. Redo. You comin’ with Gabe?”

This time, his rambling earned a full-out round of laughter, and Dean thought his embarrassment _just_ may be _worth it_.

“Yes, I’ve been discussing details with Gabriel, but nothing has been set in stone. We can talk about it more when you’re sober, and I know you actually mean these things, all right?”

“Course I mean ‘em!”

“I think you do too. But you may not be thinking about your schedule, and being impulsive.” He could basically _see_ the impish grin spreading across Cas’ face. “We _both_ know how _impulsive_ you can be.”

“Shaddup. I said I was sorry. Kinda. I am, ya know.” Dean shrugged, and let his back knock against the brick of the building from where he was standing outside. “And now it’s a big joke. Which is kinda funny I guess. Dude, I just realized tonight that Anna’s your _sister_. Why didn’t you tell me any of this? I feel like an idiot.”

“So you acknowledged Gabe was my brother, and Anna was Gabe’s sister but thought Anna and I had no relation?”

“I don’t know, dude. I’m all outta sorts. You’re outta left field. And I’m… I dunno where I am.”

“At a bar?”

“Yes. That’s _exactly_ where I am.”

“Good. Go back to your friends, Dean. Call me or text me tomorrow. I have a meeting in the morning.”

“Oh, shit, sorry. Yeah, kay. G’night, Cas. Sleep tight.”

“Good night.”

He hung up, and Dean blinked at his phone. He rolled his eyes, and remembered why drunk dialing people was always a fucking stupid thing to do. Especially Cas - he always turned into another person around the man. Well, not really - a different _version_ of himself. Castiel didn’t think it was a bad thing, if anything he liked it, but it made Dean feel vulnerable. That was something he hated feeling to begin with. But when he looked down to see his phone lit up with a text, it kinda almost made it all right.

_Cas_  
 _I’m very excited to see you, and hope you wake up with minimal alcohol poisoning tomorrow_

_Sent_  
 _Gee thanks <333_

\------------

After Jo’s bachelorette party, Dean had to admit any other hangover he’d experience was _child’s play_ compared to _that_. The girls, and his binge slash emotional drinking with the Cas fiasco at five in the morning had made him have to pull over the Impala _multiple_ times to puke along the side of the express way. Jo had gotten so fed up with him on the way back, she’d convinced him to vomit into a cup while _driving_ , because they’d never make it back at that rate. It was only his love of Baby that made his aim perfect, and he didn't make a mess. Dean felt like a stupid teenager, raiding someones parent's liquor cabinet and drinking whatever he could get his hands on to get wasted.

Still _this_   _current_ hangover… was a _close_ second.

Damn Benny and Jo and their high tolerances and love of bars.

Yep. _Those_ were Dean’s kind of people… and there was a reason they were all such good friends. Even if he woke up feeling like _this_.

He woke up in a hallway. He wasn’t sure _who’s_ hallway it was, because he never paid much attention to hallway decoration much to _begin_ with. But what kind of weirdo did, right?

He groaned and rolled on his back, his body _aching_ and head _throbbing_. At least he didn’t blow chunks in the middle of the night. The carpet surrounding him was an ugly beige, but in _pristine_ condition, none the less. Who had ugly beige carpet? Then, _someone_ kicked his shin.

“Up and at ‘em!”

It was Sam, sipping a cup of coffee, looking down at him with a grin.

But this wasn’t Sam’s place.

He was glad his brother was here at least.

“Why am I on the floor?”

“You said you were ‘ _camping_.’ You wanted to go outside, but no one would let you, so you had to figure out a way to ‘rough it’ in here. You tried to build a goddamn _pillow fort_ , but we needed those for everyone who crashed so you army crawled your way here and passed out.” He snorted, “Just be happy we didn’t draw dicks on your face, dude.”

Dean rolled his eyes and tried to slowly get up, “Where are we?”

“I picked you up,” Charlie skipped in front of him and reached out a hand to help him to his feet, “And daaamn were you _smashed_ last night.” She wiggled her eyebrows, “I took your phone away before you could do any more damage.”

“ _More_?” Dean could feel his eyes go wide, “There was damage to _begin with?_ ”

“Ohhh yes,” Charlie reached into her back pocket, “I was tempted to delete the messages to ease the burn… but figured you’d need the information for future reference. I’m an amazing friend, I know!”

Dean gaped as she placed his phone into his palm and glared at the device like it had killed his goldfish. He didn’t know if he was ready for this… if he was… “Who did I damage?”

Charlie threw her head back and laughed, “That’s for _you_ to find out. Want some coffee?”

“Can I drown myself in it?” Dean muttered and followed her, sulking into the kitchen. “I can’t even-”

“White-girl-' _can’t-even_ ’ or I-didn’t-finish-my-thought-' _can’t-even_?’” Charlie asked over her shoulder and she pulled out a mug. “Don’t worry. There’s cute stuff on there too.”

“Did you read through all my message?!” The man leveled her with a deadly glare, which didn’t seem to phase her in the least.

“I was looking out for you, of _course_ I did!” She placed a hand on her hip and answered with a glare of her own, “I didn’t hack your twitter, or anything, if that’s what you’re worried about. There aren’t any nudes on the internet, I merely read the texts to make sure you didn’t do any irreparable bridge-burning. Hah, I made a funny. You'll know, when you read 'em.”

The coffee which was set in front of him scalded his tongue, so he set it down with a clunk and dared to click on his phone. He was hoping it was dead, so he could put off scrolling through until he got home. No such luck - apparently Charlie was one step ahead, and had charged it for him during the night. A haughty ‘ _100_ %’ stared back at him, loud and proud. He groaned and clicked to the messages.

The victims last night were none other than Jo, Gabe, Meg (what the hell) and, _of course_ , Cas.

He remembered _calling_ Cas and waking him up, vaguely, but _apparently_ his harassment didn’t stop there, since he had sent his last message to him at… _5:15am._

_God_. That was probably when he was fucking _waking up_ for his damn _job_.

Why did the bachelor party have to be on a damn Wednesday?! Oh, yeah. The wedding was that weekend. Which left little time for damage control. Shit, shit, shit.

He couldn’t brave reading through the texts he sent Cas yet, if he _ever_ planned on it, really. So he settled on reading through Jo’s.

Those consisted of complaining about how her fiancé wouldn’t stop shoving shots in his face, and how he was just as bad as her. He blamed the two of them for giving him liver failure in the near future. She teased him relentlessly about not being able to hold his liquor, and told him to make sure Benny didn’t make out with any strippers. To which Dean maturely responded, ' _Ur a stripper_.’

All right, that wasn’t _so_ bad.

The majority of texts to Gabe made him _cringe_. He demanded to know WHY Anna was Cas’ sister. Which Gabe gave a _graphic_ description of their parents boning to create him, Cas and Anna, and apparently one more sibling named Balthazar? Great. Then Dean went off about how Gabe and Dean couldn’t be friends because their 'trust bridge' had burned (there was Charlie's pun) into the ocean (because apparently drunk Dean thought they built bridges over oceans), or other things that didn’t make sense, which led to Dean admitting (through Gabriel’s sneaky manipulation of Dean’s drunk brain) that he’d like to marry Cas, and he didn’t want flowers at their wedding 'because he was allergic.'

_Fuckin’ great._

He had no idea _why_ he texted Meg. Dean hadn’t talked to her since the bachelorette party, and didn’t even know she was a _contact_ in his goddamn _phone_. She must have put her number in there without him noticing, because, let’s be honest, if there was a good time to hijack his phone, it would’ve been _that_ night. And _eww_ they had _girl talk_. Like, _disgusting_ (yet clever) _gay BFF soul-searching girl talk_. They talked about how they should convince Jo to let them walk together at the wedding because they _bonded_ and they were _sassy_ and _cute_. They discussed an argument her and Ruby recently got into, and Dean walked her through how to make up. Since when was he any good at relationships to _begin with?_! Why was he giving her advice?! And, god, they even discussed the _meaning of life_ , and _their place in the universe_. Shoot him now.

Just then, a message came through from Meg. It read:

_Sorry. We were both drunk last night. Let’s pretend none of that ever happened_.

Dean flushed with embarrassment:

_Done_.

Gross. Feelings and bonding with Meg. _What_ did he drink last night?! He even went as far to delete those from his phone (destroy the evidence), then remembered Charlie had read them. He looked over his shoulder to see her knowing smirk.

“You freaking out over the Meg texts, or the Cas texts yet?”

“Shut your whore mouth.”

“Interesting,” she winked, “Carry on.”

Dean turned back to his phone, his thumb hovering over the thread of texts with Cas. Motherfucker, he was awkward enough over the _previous_ ones, and if Charlie said they were as _bad_ as the ones with _Meg_? He wasn’t sure he was going to be able to deal with this.

He finally bit the bullet. And when he did, he had to scroll up _multiple pages_ because, apparently, he was a goddamn chatty Cathy. It wasn’t just one-sided conversations, either. Fuck, he had literally kept Cas up _all damn night_ with things like “Caaaas cme bcak,” “m bored,” “Wake upp nda talk 2 me!!” Until Castiel _finally_ did. And whenever Cas went _five_ goddamn _minutes_ without responding, Dean would start again with the harassment and “dnt slep” "‘s ruuude.’"

But being an annoying fucking _child_ wasn’t the _worst_ of it. Apparently, he found it _imperative_ that he kept Castiel up to date with _all_ the conversations he was having with the rest of his friends. He’d inform Cas (in jumbled, intoxicated English) things like “ur bros blatzr?” (Cas would respond patiently - _Yes, he’s a few years older than Gabriel and I. He’s living in London._ ) And “wre not gonna hve flwers @ our wdding m allrgc” (“ _The pollen in sunflowers is too heavy to spread, and therefore decently hypoallergenic_ ) and “ruby n meg hada fight lets not fght again” (“ _I hope we don’t, Dean_.”)

And Dean was _mortified_.

He couldn’t even type back and apology, and sure as shit, Cas’ last text was “ _Get to bed, it’s late. I need to get ready for work_.”

“Fuck!”

“Now _there’s_ the Cas-text-freak-out I was looking for!” Charlie giggled and pecked Dean on the cheek, “I think sunflowers would really bring out your eyes. For the record.”

\-------------

Benny’s best man was out of state, so although _he_ was supposed to be helping out with all of the wedding errands and general chaos, it was delegated to _Dean_. Which he took as a welcome distraction, because it was Thursday, and that meant Cas was flying in with Gabriel tomorrow night. He was nervous as hell. Although Cas had brushed off all of Dean’s stupidity, Dean felt just that - like a _moron_.

How many times was he going to act like an absolute _idiot_ in front of the man until he left for good? _How_ hadn’t he scared him away, already?!

So, here he was, picking up all the groomsmen’s suits, and balancing garment bags while Benny read off a list.

“Dammit, I love Jo, but her handwriting could really use work,” he groaned, as they started loading up the Impala.

“Well, lucky for you, I’m nearly fluent in that chicken scratch,” Dean announced proudly as he took the list. “All right, garb, done, decorations, done. Now I think you’ve just got a bunch of checks to fill out to the DJ and photographer and touch base with them for times Saturday, right?”

“Ehh, sounds about right,” he groaned, “Why does this have to be so damn expensive? Shoulda just eloped in Vegas. That’s what you should do, Dean. Take it from me, this is _rough_.”

“It’ll be worth it, man,” Dean clapped him on the back. “’Sides, the way Jo glows like a fuckin’ _fairy_ every time she talks about it? You’re making her happy, dude. And even if it’s a lot of dough, it’ll be worth it when you see her light up at the end of that aisle.”

“When did you become such a romantic?” Benny raised an eyebrow, but the look on his face with even more sappy than Dean’s words. “Who are you, and what’ve you done with Winchester?!”

“Saw it on a movie,” Dean huffed, quickly, “Ya know, Sam’s favorite channel is Lifetime.”

“Yeah, right. This have anything to do with a certain someone Jo told me all about?” He raised an eyebrow and snatched the list back from Dean. “Don’t be shy!”

“You guys have anything better to do than gossip?” Dean groaned, and would have bantered more, but his phone vibrated.

“Nailed it,” Benny sounded pleased with himself. “ _That_ stupid look on your face. I knew it. I see it in the mirror on the daily basis, so if _I_ can admit it, _you_ sure as hell can, too.”

The man glared, but it was halfhearted. So what if the text _was_ from Cas? So what if the dude made him happy, that shouldn’t be anything he had to defend or explain! He didn’t like the way Benny was cornering him and teasing him.

But he _did_ like the way Cas texted him ‘ _Our arrival time is 8:20 tomorrow.’_

Yeah, Dean _knew_ he was cheesing, and he didn’t _care_. He _also_ didn’t care he was ignoring Benny and responding, ‘ _We should be done with the rehearsal dinner by then. Want me to pick ya up?'_

_‘If you’re free. If not, we can take a cab, it’s no problem.’_

_‘I’m picking you up.’_

_‘Thank you’_

“Earth to Dean?”

“Sorry, just talking about when his plane gets in, that’s kinda important Benny,” Dean rolled his eyes at his friend’s smirking face.

“So, T minus how many hours ‘til magical reunion sex tomorrow? Know your countin’ down.”

“Whatever. Let’s drop these off and call up Ellen to see if she needs any cash for catering help. Damn, it’s nice to have a cook in the family. This is gonna be the best wedding ever,” Dean was salivating at the image of Ellen’s food. “We should just go to the Roadhouse and ask in person. And grab a burger. And onion rings. And a beer.”

“I think that’s a good idea, brother.”

\----------

The funny thing about this whole wedding was that if Dean had a vagina, he would most _definitely_  have been Jo’s maid of honor. Which was why he had accompanied Benny to all the manly groomsmen activities, and was _now_ bored out of his mind, sitting in a bridal boutique watching Jo getting the final touches put on her dress. Which was where he found himself Friday morning.

And it was just a handful of hours until he saw Cas again…

He crossed his legs and sank in his seat, while Jess and Lisa were on the edge of their’s, aww’ing and giggling with excitement.

“Have you decided whether or not you want the blusher?” The woman zipping the dress up, inquired to Jo.

“A _fluffer_?!” Dean demanded, jolting out of his seat.

“ _Gross_ , Dean!” Jess punched him in the arm. “You’re confusing real life with porn _again_!”

The professional’s cheeks turned pink at the comment, and Jo stuck her tongue out at Dean, “It’s the veil Benny lifts up after I walk down the aisle, jackass.”

“Yeah, you _should_ probably get it. Cover that ugly mug up as long as possible,” Dean winked, “You’re lucky you’ve got a bangin’ bod, at least. Your ass looks _great_ in that dress.”

Jo ignored the ‘ugly’ comment, and instead shook her butt in the mirror to prove Dean’s point. “Touche, sir. _Touche_.”

“Now the _important_ question,” Lisa leaned in, and whispered conspiratorially, “Can she twerk in it?”

A wicked smile crossed Jo’s lips, and the woman helping them in the dressing room quickly yelped, “Is there anything _else_ I can help you with!?” before Jo could pull up the dress to answer Lisa’s question.

The bride pouted, knowing her fun was ruined but shrugged, “I think we’re good. And I’ll take the blusher, just because I think it’ll be _hilarious_ to see Benny and his big, beefy hands try to be delicate with it.”

“You’re cruel, Joanna,” Jess giggled, but approved of her decision. “Extra points, if he tears it on accident.”

Lisa raised her eyebrow, “You’re counting _points_ on ways your _wedding could fall apart_?”

With a shrug, Jo simply flashed a toothy smile, “Where’s the fun in counting the ways it goes _right_? _That’s_ a win all by itself. If shit hit’s the fan, we can at _least make bets_ as to _how_ it’s gonna hit the fan, and someone will _win_ that way. See? Find something positive outta the negative. I'm a goddamn genius, I know!”

“In that case,” a strangely _evil_ grin appeared on Lisa’s usually innocent face, “I bet _ten_ points Dean leaves with Cas _before_ the wedding’s over.”

“Hah! I bet he leaves _after_ the toast, but _before_ the dollar dance,” Jess chimed in immediately, clapping her hands together.

“You’re betting on _me_?!“ Dean gaped, “You’re _seriously_ doing this right now?! I have self-control, you know!”

“Amateurs!” Jo grandly gestured to the room, spreading her arms wide and raising her voice, “ _Fifty points_ Dean and Cas will be _caught_ trying to bone _at_ the wedding, and end up being kicked out _before_ the bouquet toss!”

Dean was gritting his teeth and growled, “ _One hundred points_ we’ll stay the _whole goddamn wedding_ , you _assholes_!”

The three women blinked, and then looked at each other, simply _ecstatic_.

“Your funeral, Winchester.”

Then it hit Dean, that in a moment of _anger_ he’d _blindly_ made a _bet_ with these _heathens_ , acting before thinking, that he _wouldn’t_ jump on Cas the first chance he got. People left weddings early all the time, and no one batted an eye. But he just _promised_ to stay through the _entire thing?_! Without molesting Cas?! What the fuck has he done…

\-------

After the dress fitting, Dean sulked back to his apartment. He had a few hours before the rehearsal and rehearsal dinner, and wanted to collapse on his couch to kill a little time. His stomach rumbled, and the gave in to the urge to fix himself a quick snack before he made due with waiting in front of the TV. Half-way between making a PB&J, his phone rang.

Not _text_ -rang.

_Phone-call_ -rang.

He frowned and sat down the knife currently coated in peanut butter, to see Cas’ name lit up on the screen.

“Heya, what’s up.”

“Hello, Dean,” his voice sounded pinched and tight.

“You all right, man?”

“I’m perfectly fine. But the plane I was going to take _apparently_ has some problems with the fuel tank and they won’t be able to get a replacement flight until early tomorrow,” he sighed deeply. “I’ll be able to make the wedding, but I’m afraid I won’t be in Kansas until 7am.”

Disappointment spread through Dean’s chest as he leaned against the counter and rubbed his forehead, “Hey, there’s nothing you can do, ya know. Unless you hijack another plane and change the course, but I don’t think I have the skill set to bust ya outta jail. Just saying.”

The man laughed lightly before confirming, “I don’t think _I_ have the 'skill set' to hijack a plane, either. So I don’t believe that’s an option.”

“Sucks, dude,” Dean admitted and sighed, “Not gonna lie, I was looking forward to seeing you tonight.”

“I was as well,” he could hear the sincerity in Castiel’s voice. “If I was closer, I’d drive but I don’t think that’d be a good choice, at this point.”

“Where are you, even? You’re always elusive and mysterious when it comes to answering my questions. It’s like you’re a spy, and if you tell me you’d have to kill me.”

“Nothing _that_ intense, I can assure you. I’m in upstate New York, currently. It’s a small airport, unfortunately, and there aren’t many flights headed to Kansas and they’ve assured me this is my only option, no matter how much of a fuss I’ve made.”

“Aww, did ya make a scene for me, Cas?”

He actually laughed at this, “There _may_ have been a few choice words upon check-in, but only because their manners were sub-par at best. It should be considered as a lesson.”

“Oo, you make me _tingle_ when you get all _bossy_.”

Dean could see the man raise an eyebrow, “Is _that_ all it takes?”

“From _you_ , maybe.” He shrugged his shoulders, even if Cas wasn’t aware of the movement. “Well, I’ll set my alarm to wake my ass up to get you in the morning, I guess.”

“I’ll let you know if there are any other delays, but I would assume there won’t be.” Cas paused, “I’ll text you my new itinerary.”

“Sounds good. Be safe, and stay out of trouble.”

“Same to you, Dean. Have fun at the rehearsal.”

“See ya, Cas.”

When Dean hung up, the disappointment fluttered through his stomach even more and he glared at his phone. Upstate New York, huh? He _still_ didn't know much about Cas. He was fussy, and could feel a foul mood coming on, now that he knew he wasn’t going to be able to see the man tonight.

What only _increased_ his foul mood, was the bet he made with Jo…

If he couldn’t see Cas tonight, and the first time he’d be reunited with the man was _right_ before the wedding, how the hell was he supposed to _keep his hands to himself_ the entire day?! Now he was _more_ than screwed. He _wanted_ to throw his phone across the room, because the impending sexual frustration was a _dangerous_ thing, and he knew it was only going to get _stronger_.

But… if Cas _wasn’t catching his flight_ , that meant he _wasn’t doing anything, right_? He’d just be _waiting_ around until his next flight tomorrow. The more Dean thought about, the more he was _convinced_ that there was only one _logical_ thing to do. So, he picked up his phone and sent a message to Castiel.

_So Cas. What are you wearing?_


	4. Chapter 4

Dean waited by the phone to see whether or not to abandon his peanut butter and jelly for more _interesting_ activities when the screen lit up with a message from Castiel. Ok, fine, 'what are you wearing' wasn't exactly an original line or anything, but it got his point across. At least he was optimistic.

_Cas  
An annoyingly stiff suit, jacket, and a seat belt currently._

Then another message:

_Cas  
Would you like me to take off more than the seat belt when I get back?_

Dean huffed a laugh and could nearly _see_ Castiel raising a cocky eyebrow as he suggested the words. But instead, Dean responded:

_You better not be texting and driving buddy_

_Cas  
I’m in a cab five minutes away from my hotel. You’re answering your phone when I arrive._

Fuck the PB&J.

Dean was giddy as he quickly wrote back: _Sir yes sir_ \- and screwed the tops onto the containers and put them back. He wasn’t about to jam the sandwich in his mouth and risk choking to death before Cas called him in the excited anticipation, so he left it on the kitchen table and scurried into his bedroom.

He kept his eyes on the time - did Cas mean _exactly_ five minutes? Or was he just hinting that'd it'd be a hot sec? He was counting down, regardless, and this was basically the longest fucking five minutes of his entire goddamn life. Dean could feel his cock twitching in his pants at the aspect of having fucking _phone sex_ with Castiel - the guy _already_ sounded like a phone sex operator - and hoped he wasn’t getting jerked around.

Dean was obvious enough, right?

And he was horny. Really. Really. Horny.

He groaned and rolled to his side as he glared at the phone - needing it to ring. But it kind of had the _same_ effect as watching water boil, really…

… except boiling water never gave him a goddamn boner.

Thank god, the phone _finally_ rang!

He exhaled to calm himself, and tried not to snatch it up and answer before the first ring was over.

Yeah, so he let it ring... twice.

And probably _still_ sounded _way_ too eager.

“Seat belt off?” Dean greeted, then rolled his eyes. Smooth introduction, there, Winchester. Really smooth.

There was a low, rumbling chuckle on the other line as the man confirmed, “Yes, seat belt’s off. I’m walking through the lobby now.”

All right, so at least Dean wasn’t the _only_ eager one, _right_?

“Aww, Cas. Wanna get your phone sex on in public?” He teased, and wondered who was around the man as he walked to his hotel room.

“So I assumed correctly,” there was a shy (obviously fake) quality in the way he spoke, “In that case, I told you what I was wearing. Return the favor.”

While sprawled out on his back, Dean’s eyes glanced down because, if he was honest, he had _no idea_ what he threw on that morning. He’d been planning on changing before the rehearsal into something that _impressed_ Cas when he picked him up, so whatever he was wearing now was an early-morning coffee-less zombie concoction. So he kind of _skimmed_ on the details.

“Jeans, a t-shirt and an old hoodie,” Dean paused and then added suggestively, “Things I wouldn’t mind you tearing off me this time.”

“Oh, you mean you were attached to _that_ dress shirt?” Castiel hummed. “It looked stunning on you. But even more so, ripped apart and on the floor.”

Dean would have admonished him because, _yeah_ , he _did_ like _that_ goddamn shirt (which he was still in mourning about) but Cas’ words sent a tingle down his spine. “I’d like it more if you were ripping _this_ shirt off me right now.”

“You should take off the hoodie so I’d have better access to the shirt,” his voice was casual and Dean could hear a door unlock from the other side of the phone.

Cas must _finally_ be in his hotel room.

_Hell yes._

“I will if you do the same with your jacket.”

“Already done.”

So Dean immediately yanked the hoodie over his head and flung it some place across the room. He settled back on the bed and began to visualize the way Cas wore a damn suit last time. The way it was tailored to his body, made his shoulders look strong and presented him as all kinds of dapper but did _nothing_ to hide the _awesomeness_ that was underneath it… fuck, Dean wanted it again. He wanted it _now_.

“Where are you, Dean?”

He cleared his throat and admitted, “I’m in my bed.”

“Good,” there was a devilish tone to his voice. “Right where I want you.”

“Tell me _more_ about what you want, Cas,” Dean mumbled, because he _needed_ to know.

The man just _did_ things to him. Made him let his guard down, drove him _crazy_ and _took control_ in the fucking hottest way Dean _never_ even knew he _craved_. Through both his touch and his words… and if he couldn’t have his touch right now, he sure as hell was gonna get the other.

“I don't want you to stop with the hoodie. I want you naked. Completely naked and on top of the covers. I want you all spread out for me and waiting for my order. Can you do that?” His voice was pitched lower, and there was a rustle of fabric from the other side.

Dean wasn’t sure if it was him getting into bed, or some other kind of clothing coming off, but he didn’t care. He had a job to do.

He mumbled a confirmation, and went to work peeling off his socks, sweatpants (he’d _totally_ lied when he said he was wearing jeans but didn’t want to sound like a fuckin’ bum) and boxers in one go and then his shirt. Dean _did_ want to climb under the covers, it was _damn cold_ in his room because he refused to turn on the heat, but Cas told him to stay like this so he did. He pulled the phone back to his ear.

“Waiting,” Dean proudly confirmed his nudity with a grin, but then asked, “Are you stripping down too, babe?”

The word slipped out without him meaning it to, and he winced. Cas didn’t seem to notice and slash or mind, because he didn’t acknowledge it.

“No. I don’t need to remove my clothes to take you apart. I’d have you stretched out in front of me, watching the way your toes curl or your legs quiver when I have my way with you,” he hummed. “The way your body flushes when I barely touch you… when I kiss every part of you. Use your fingertips, Dean. Brush them down your neck, over your chest and against your stomach. As though it’s me who’s touching you.”

Dean gulped a little, and although this wasn’t the usual ’jerk yourself off’ phone sex, he’d go with it, because Cas’ voice and the images already had him getting hard in record time. He had never touched himself like this, so it was _awkward_ … but when he thought about it like Cas had said - _like it was Cas_ \- his mind went back to the night they were together and pieced the touches from then and now - assembling them like a puzzle. He made the pieces fit. Dean sighed into his own feather-soft caresses and admitted, _okay_ , that was _nice_.

“I’d take my time,” Cas continued, “Pressing my mouth over _every inch of you_. Tasting you, and sucking marks into your skin. Just the right amount of pressure - with my teeth, making you moan and leaving marks that told you you’re mine. Trailing down your throat, nipping at your hip bones and kissing low on your stomach as you squirm underneath me.”

He couldn’t help but moan, just like Cas said he’d make him, as he swiped his hand across his stomach and brushed the head of his cock. Dean wanted to take himself into his hand, but _knew_ he wasn’t supposed to yet, this was all part of the game, right?

“Want it bad, Cas,” he said instead, trying to keep his hands above the belt. “Like it when you’re a little rough. It does things to me.”

“If you encourage me to get rough, I’ll be _more_ than happy to deliver,” there was a rawness and desire in his voice. “I get drunk off the noises you make. I get _greedy_ and _want_ more, and I know when I finally taste your cock you’ll make the most delicious sounds. So I wouldn’t hold back. I’d suck the head, finally get a taste of you, and I wouldn’t be able to stop until you were down my throat.”

Dean cursed under his breath and moaned, “Goddammit, Cas. I need your mouth on me, wish you were sucking me off right now. Can I touch myself?”

“ _Not yet_ ,” Cas ordered instantly. “Tasting you would never be enough. But I’d enjoy every second of watching you writhe and beg before I needed even more.”

Castiel’s voice was shaky over the line, and he was breathing a little harder.

It was a _miracle_ Dean _hadn’t_ touched himself yet - he was leaking precum and instead of ‘gently caressing himself’ or whatever the hell Cas told him to do before, he was now gripping the blanket with his free hand to keep his shit together.

“ _Cas_ ,” Dean groaned. “Let me touch myself and imagine it’s your mouth-”

“Did you like it when I tongue fucked you?”

The question punched the wind out of Dean, because _that_ was a question he had not been expecting.

“Y-yeah. _Shit_ , Cas, I liked _everything_ you did to me. You kinda popped my cherry on that one... and I thought it would be weird but it was kinda awesome.” He admitted and was glad Cas wasn’t there, for the first time, to see him blushing like a school girl.

“Good,” he cooed. “Because I’ll be doing that _over_ and _over_. The way you went from curious to needy at the tip of my tongue was beautiful. I’d be flipping you on your stomach right now and spreading you wide open. Do you have lube, Dean?”

He whimpered and couldn’t even form thoughts for a second, let alone _words_ \- until he finally did, “I think-”

“Get it, then put me on speaker.”

Dean cursed and ungracefully rolled nearly _off_ the bed to grab what he’d actually bought _specially_ for _this weekend_ and thanked his lucky stars he had the foresight to open the seal and everything. He clicked the call to speaker and laid back down, breathing heavily and asking Cas, “Got it. Do you want me to…?”

He let the thought hang in the air, waiting for more direction.

“W-Want you to slick up one finger, Dean, get it nice and wet,” there was a _definite_ zipper-noise on the phone. “Just _one_. Trail it between your legs and tease at your hole. _Don’t_ go in too deep, _don’t_ finger yourself. Save that for _me_ tomorrow. Right now, imagine it’s my tongue, fucking you between your legs.”

Dean very, very eagerly did just that. He shuttered and moaned at the contact fucking _finally_ , but it was another form of _torture_ to not be able to finger himself already. He had done that enough times already, thinking about Cas’ cock inside him, and it took him all the will-power and self-control in the world to _not_ just dive in. Still, it felt fucking great.

“Get more lube, Dean, and cover your other hand,” Cas ordered, his voice getting rougher by the minute. “Use that hand to touch your cock.”

_Hell yes._

“Are you touching yourself, Cas?” Dean asked as he poured more lube from the bottle, because he _needed_ to _know_.

“Y-yes. Just _thinking_ about eating you out while stroking your cock got me too hard. I want to cum with you,” Cas moaned out, “I’d get you off like this, licking you deeper and deeper while you thrust into my fist, begging for it, begging for _more_. Right when you were on the brink, I’d wrap my mouth around your cock and finally reach down my pants to my aching erection. You’d be crying out, _needing it_ more than _anything,_ and I’d give it to you. I’d jerk off and make you cum, screaming, and suck you _completely dry_. W-Would you let me cum on you-?”

“ _Fuck_ , Cas, _yes_ , I’m cumming now,” Dean _couldn’t_ hold back anymore, he had been on the brink and _Cas_ ’ fucking _dirty mouth_ and the final touches sent him over the edge. He couldn't control the noises he was making - didn't want to, he _wanted_ Cas to know what he did to him, _hear_ what he did, how hard he was cumming. His throat was raw as his orgasm knocked him on his ass. 

He came all over his stomach, his rocking upward thrusts winding to a close as he heard Cas on the other line panting, and finally moaning his name too.

Dean was left to catch his breath, a boneless heap in the middle of his bed, and he suddenly realized that, _shit_ , he was _alone_. That entire time, he’d _honestly_ felt like Cas had been there _with him,_ and now it was a fucking bummer he didn’t have the man to cuddle with. But… hot damn. That was _not_ what he had been expecting. And he voiced it:

“Shit. Fuck, Cas, you’re _really_ something…”

The other man had probably nodded and chuckled. “As are you, Dean.”

“Goddammit, I want you here, _now_.” He didn’t care if he was whining, that’s honestly how he felt. “Tomorrow can’t come soon enough.”

“Did you just make a pun?” Cas teased, and Dean could hear another rustle of fabric. Probably the clean up.

That made Dean grin like a dope. He wasn’t sure why, but everything about Cas just made him _giddy_.

“Shush. I’m punny as hell.”

“I’m glad you messaged me, Dean,” there was a warmth in his voice, not _just_ that after-glow warmth. “We’ll talk soon, all right? Don’t you have a rehearsal to get ready for?”

“Yeah, that _thing_ ,” he chuckled. “Thanks to you, I’m in desperate need of a shower. In a good way. Very, very good way.”

There was a deep laugh and he agreed, “Same here. Have a good night, and I look forward to seeing you in the morning.”

“You too,” he quirked a smile (thinking about earlier and then said _fuck it_ ) and added in, “Babe.”

\--------

There were a couple raised eyebrows that told Dean he needed to get the skip in his step under control when he walked into the rehearsal. Luckily, it was only Team Awkward (Garth and Hannah) who wouldn’t be able to make a cutting jab if their life depended on it. Unfortunately, Garth took his good mood to mean he needed to be hugged _immediately_. Which had Dean rolling his eyes and patting him on the back twice to get the man off him.

“Heya Garth,” he tried to smile politely, when the man lingered a little too long.

Then, it turned into Dean forcibly _peeling_  him off.

“Whoo-wee! How ’bout that bachelor party, Dean?!” Garth got a dopey grin across his face. “That was wild!”

“You act like you’ve never seen a stripper before, dude,” Dean rolled his eyes, and noticed Hannah blushed red and turned away abruptly.

Oh, he’d have to get some liquor into her again, soon. She was a riot when she was drunk. Now… _not_ so much.

“Hush, Deano,” Garth playfully smacked him, “I’ve seen naked women before. And boobies. Lots and lots of boobies.”

As much as this was the _perfect_ time to tease the man mercilessly and call his bluff, Dean refrained. After all, he really _was_ in a damn good mood. So he settled on winking, and walking into the room where Jo and Benny were hovered around another one of Jo’s un-readable lists.

Dean huffed, and snatched it out of her hand, grumbling out, “Did you not pass first grade or some shit, Joanna?”

“I’m beginning to wonder that too, brother,” Benny groaned, “Don’t ya’ll do this on your fancy phones these days anyway?”

“Hey! I got this stationary from my great grandma, I needed to use it!” Jo snapped, and smacked Benny hard on the arm.

“Woah woah, no need to Bridezilla it,” Dean ruffled her hair, which earned him a glare, but asked as he read the list, “This is who’s walking with who, right?”

“Yeah.”

“All right, let’s line up, then!”

Benny worked with Dean at the precinct, so he knew all the guys before hand, and had gotten _uncomfortably_ familiar with the girls after Jo’s Chicago adventure. He also knew Benny didn’t have as many friends as Jo, so he had to scramble his ass around to _find_ enough people to fill the spots. Thankfully, Miss Joanna Popularity Harvelle had _more_ than enough guy friends to go around too.

As they lined up, Dean swallowed hard when he realized that he _wasn’t_ paired up with Meg, as the two had girl-chatted previously, but fucking _Anna_. Who was shooting him judge-y looks.

Fan-fucking-tastic.

Even though Dean was dubbed ‘Jo’s maid-of-honor- among their friends, for the sake of the guest and wedding photos, that responsibility fell to Charlie - who was walking with Benny’s best man, and former partner (before he changed stations) Victor. Dean and Anna were lined up right behind them.

She gave him a polite smile and stated, “Very kind of you to pick my brothers up, Dean.”

Dean jumped when he felt a hand smack him _hard_ on the ass, and turned around to see Meg grinning at him from behind. “Both of them? At the same time, I hope? You kinky bastard!”

“Shut up!” The man snapped, and noticed Anna did little more than roll her eyes.

Yeah, they knew each other _too well_ at this point.

“Fancy seeing you here,” Meg cooed and winked, “Glad I get to stare at your ass while I’m walking with little Winchester. Where is he, by the way?”

When he looked over he noticed that Sam, indeed, was missing. Dean raised an eyebrow to Jo, who was reading the list out, and answered, “Running late, I guess. Rude.”

“Speaking of, when does Castiel get in again?” The redhead asked, turning her attention back to Dean. “I know his plane was delayed.”

“Morning, I can forward you the flight info, if you want?” Dean felt fifty shades of awkward, and just _knew_ he was getting sister-vetted as they were speaking.

“Cas is gonna be _late_?!” Jo’s eyes lit up and she stopped reading from the list.

“Yes, there was an issue with his plane. Why?” Anna turned her attention to the blonde.

“Nothing. That just,” Jo’s lips pressed together tightly to control her giggles. “ _Sucks_ for Dean. It’s gonna be _hard_.”

No, nope. He was not gonna rise to that bait. Hell no.

“Get on with the list!”

\-------

When Sam showed up, he wished that he _hadn’t_ , because he felt like a goddamn _home wrecker_. Becky Rosen was walking behind him with her boyfriend, Chuck, but she couldn’t stop making goo-goo eyes at him and (as Charlie called it) fan-girling? He didn’t even _know_ what that meant, but he felt like that verb was something that worked.

Even if Dean couldn’t see many of the other couples behind his gigantor of a brother, he could fucking _hear_ Crowley and Ruby. They were bantering, and speaking in a language of insults that Dean couldn’t even _keep up_ with. Their tongues were sharp, the words smooth and each one cut the other _deeper_. Honest to goodness, if Dean hadn’t known Ruby was head over heels for Meg, he would have laid down money on hate-sex between those two, any day. Even if it was disturbing.

When Dean had asked Sam in a hushed whisper, just who the fuck Crowley was, Sam just responded back that ‘Benny and Crowley made a deal.’

Or… whatever the hell _that_ even _meant_?

Lisa and Garth were strangely silent, in between the Hell-Duo and Bela and Ash’s avid discussion of the latest ‘Snapped’ marathon, and how they'd have better (strategically) gotten away with murder. Apparently, they were using _their_ brains and cunning for day-time reality TV? Which left Garth making doe-eyes at Lisa, and Lisa suddenly fascinated with her phone.

After the first debate between Bela and Ash about a wife shooting, then butchering her husband and burying him, Kevin piped in with facts about the decomposition rate in the soil, and Dorothy spoke of the caliber gun and gun powder.

Dean _knew_ if a body went missing anywhere around Lawrence, _those four_ did it and they’d _never_ find it. Cold case, right out the gate.

The last three couples were casually chatting and getting to know each other. Jessica already knew Adam, who happened to be Dean and Sam’s half-brother who Jo dated for a brief stint in high school. They figured out they were better as friends, and he turned into her family right away. Jess was asking Adam about his first internship, and he was quizzing her about her new job. Relatively tame stuff, considering the rest of the bridal party was full of _crazies_.

Hannah was walking with Samandriel - one of the newbies at he station, who Benny had taken under his wing about a year ago. He regularly ate at the Roadhouse, so when Benny was getting nervous about finding enough groomsmen, Ellen had suggested, “How about that shy kid with the weird-ass name,” since that’s _exactly_ what Benny was looking for in a groomsmen? But he loved the kid, all the same, and to be honest he was two seconds away from putting a damn ad out on craigslist. And when he asked, Samandriel’s eyes lit up like he’d won the lotto, and it made it all worth it.

Of course, that’s when _another_ one of Benny’s friend’s, Gadreel (speaking of funny names, everyone called this one Zeke - who knew why) demanded why _he_ hadn’t been invited, which was even _more_ uncomfortable because Benny was about to ask him anyway. So, Zeke was walking with Tessa, and that rounded off the line.

Dean wondered if they needed a role call or attendance sheet, come actual wedding day, because this was _ridiculous_. Were there even people _coming_ , or was the bridal party the _whole_ damn _wedding_?! He groaned and straightened his posture, as Bobby snapped at them all to get their shit together so they could get this over with and then have a damn beer.

And that’s why he loved Bobby so fucking much.

He couldn’t have been happier when his surrogate dad fell head-over-heels for Ellen, and now Jo had someone to walk her down the aisle.

He’d be damned if Bobby got out of it with dry eyes, the old coot.

They went through the motions and steps, incorporating lots of ‘blah blah blahs’ with ‘and thens’ until they made three loops around and figured they were _experts_ at how to walk two-by-two. Like - if the flood came, and anyone built an arc, they'd be the first ones to put up a tutorial video on YouTube. Instantly viral, too.

Garth’s stomach growling obnoxiously loud when they were goofing around with the ‘you may kiss the bride’ part also affectedly ruined the mood. And thank god the Roadhouse was less than ten miles away from the venue they’d booked, because Dean was in need of some red meat -  _pronto_.

They carpooled where they could, Sam, Charlie and Dorothy hopping in the Impala with Dean and then they were on their way.

Dean couldn’t help but tease them while glancing in the rear view mirror, “So are you guys gonna magically catch that bouquet together complete with choreographed steps, or do you already have wedding plans?”

“Don’t be jelly I’ve got my hottie and you don’t,” Charlie poked him in the shoulder, “You will, soon enough! Patience, young grasshopper!”

“Have you seen him since the piano bar?” Dorothy inquired, leaning up in her seat. “Where’s he from, anyway?”

“Uh.” Dean didn’t like questions. He didn’t like questions at all.

“Don’t tell me you still don’t know,” Sam gave him an incredulous look. “You’re getting all melt-y for this dude, and you don’t even know where he’s from or _anything_?”

“He’s from New York. And he’s in accounting.”

So he made something up.

And it would’ve _worked_ , if _Charlie_ didn’t start cackling, and roll over in her seat from laughing so hard, “ _Dean_! He’s a fucking _lawyer_ from _California_! Are you shitting me right now?!”

“Hey!” Dean whipped around in the front seat to stare her down, “How do _you_ know this, anyway?!”

“Because I _talk_ to people, instead of jumping on their dicks. Obvis.” She rolled her eyes.

“You were too busy tongue fucking Dorothy's mouth that night to even _talk_ to him!” Dean called her out _immediately_ , while he blushed red at his _own_ idiocy. “You’re a little rat and facebook stalked or something!”

“He doesn’t _have_ facebook, although she _did_ check,” Dorothy didn’t falter in her step at the words ’tongue fucking’ the way Charlie had. “She just interrogated Anna. Quite _thoroughly_ , I might add.”

“Aww, are you jealous, babe?” The redhead nuzzled into Dorothy’s shoulder and pecked her on the cheek. “I was just doing it for Dean, don’t worry.”

“What else did you do for Dean? I mean, me. I mean-- fuck.” Dean slammed his head into the steering wheel once before he righted himself. “You know what? Never mind.”

“He’s a lawyer, lives in Huntington Beach, but jet sets all over criminy because people pay him the big bucks. He’s thirty four, originally from Russia but fam landed in the states. Super religious family, so I guess he’s kinda shy on the outside, but according to Dean, a freak in the sheets. Started off studying theology, changed it to law once he moved away from said crazy parentals. He likes bees.” Charlie rattled off, as she played with her girlfriend’s hair.

“Bees?!” Sam and Dean demanded in unison.

“Fuck if I know. That’s all Anna told me.”

Yet waaaay more than Dean knew about him to begin with. He felt like a _idiot_ , but was he _really_ supposed to be getting this information out of Gabe or Anna? He wanted to know it from _Cas_ but the man just wasn’t _working_ with him. _What_ was he doing? Really, though?

\---------

Ellen had closed the Roadhouse early and with the help of all the groomsmen, shoved a group of tables together to seat the bridal party. As much as Jo wanted to help grab the beers, she was pushed aside and ordered to sit down, this was her and Benny’s weekend, after all. Meg and Ruby gladly took on the duties, and it was fitting - since they had met Jo all working at a bar. It was efficient as fuck, too, Dean had to admit. They knew what they were doing, and mixed a _damn good_ drink.

He wasn’t even mad to see himself sitting next to Meg and Ruby once they were done serving up the first round. Dean jumped up to help Ash and Garth grab the food Ellen had made, and set it up buffet-style along the bar. Once everyone sipped their drinks and chatted, they began snagging their plates and loading them up with food. Dean’s taste bud’s were _singing_ while he was shoveling on the bacon and cheese potatoes and rinsed it down with an IPA.

“Breathe, Dean,” Sam rolled his eyes, watching his brother devour the food. “Are you stress eating? You’re not gonna fit into your suit tomorrow.”

Dean didn’t even justify him with a response, just shoved in a larger bite and chewed obnoxiously close to Sam’s face. His brother socked him in the shoulder and fake-gagged a little bit, until they realized that Hannah and Lisa were very unamused.

Then, Dean noticed that _Anna_ was unamused.

God, this whole _sister thing_ just ruined his _whole_ night.

He turned back to his food and closed his mouth while he ate, very suddenly feeling like a reprimanded child. Which he did not like at all. He _especially_ didn’t like when he was called out on it.

“Food’s not falling outta yer mouth, boy, you all right?” Bobby raised an eyebrow and took a swig of his own beer.

“Bobby, there are ladies at the table,” he winked, and then last minute, patted Sam on the head.

“Where exactly are those?” Meg sneered, and grabbed Dean’s beer. “Refill, champ?”

“Yes, darlin’!”

“ _Dean_!” Anna snapped, “You’re being _irresponsible_!”

“Wha?” He turned to her wide-eyed and fumbled with his words, “W-What are you talking about?”

_Why_ was he pissing her off? He was going out of his way _not_ to piss her off, this _wasn’t funny_! Did he not _pray_ before he fuckin' _ate_ , or something? _What_ was her issue?

“You shouldn’t have more than one beer if you’re driving,” her eyes were set like she was explaining it to a fucking moron. And Dean didn’t like that one bit.

“Uh… by the time I leave, I’ll be fine. And if not, Ellen’s got places to crash here, I’ve done it before…” he spoke slowly, like she was going to _pounce_ across the table.

“Gabe’s plane arrives in a little over an hour,” she scoffed. “I don’t plan on you getting a DUI on the way to the airport.”

“Wait- _Gabe_?”

Anna was _beyond_ annoyed at this point. “Gabriel is coming from Chicago. Just because Cas’ plane in New York was delayed, doesn’t mean Gabe’s was. They planned on arriving at the same time to make it easier on whoever was picking them up. Or were you just going to let Gabe wait at the airport? If it’s an inconvenience, I’m sure someone else would be willing to, even though _you_ were the one who volunteered in the _first place_.”

Yep.

Dean was on her shit list.

“No, I still got it. Sorry, Anna, just slipped my mind. Thought they were traveling together or something.” He cleared his throat, and looked around the table, where all eyes were on him, and had gone silent. “Drink up, assholes.”

Some laughed, some clinked their glasses telling Dean ‘sorry dude’ but Anna kept glaring. _Great_. Just _great_. Now he had to deal with Gabe too?

Such a fantastic night.

\--------

At least it wasn’t just him heading to the airport. After he’d finished cleaning his plate, and grabbed his jacket, Jo met him in the kitchen and looped her small arm around his waist. She informed him she was riding along, which had Dean more than a little confused.

“Shouldn’t you be doing, I don’t know, bride-y things? Hang out with the party?”

“Please,” she rolled her eyes, “I’ve been doing bride-y things all day. Fuck, all month, if not all year. Besides, you need someone on your side if Gabriel is going to harass you like I _know_ he’s going to.”

“Shut up, you’re going to join in,” Dean grumbled as he led the way to his car.

“Yeah. Probs. But at least my teasing comes from a place of love.” Jo walked around to get in the passenger side and quickly pulled on her seat belt while Dean took a deep breath.

This wasn’t going to be fun. He already knew it.

He needed to bite the bullet.

When he finally slid into the front seat, Jo was waiting for him, leaning back and comfortable, with an expressive look on her face.

Dean ignored her for as long as he could (which happened to be all of turning the car on, and shifting it into drive) until her stare became _too_ annoying. So he shot her a menacing glare.

“What.”

“Nothing. Just thought it was cute. How well-behaved you were trying to be in front of Anna,” she smirked to herself, “You kinda like this dude, don’t you?”

“Is _this_ why you came with me?! So I’m currently signed up for _double_ the torment?” Dean groaned and hunched back against the leather seat. “Don’t make me turn this car around, Joanna Beth.”

“Relax,” she swatted at him. “You were so chill with her at the bachelorette party, and _now_ you’re walking on egg shells trying to impress her and I _know_ it’s not to get in her panties.”

“Maybe I _am_ ,” Dean winked. “She’s hot, why not?”

“Nah, your usual approach is obnoxious bravado disguised as boyish charm. I know your seduction techniques. Plus, if you were _really_ into her, you’d have made a move at my party instead of going home with her _brother_.” Jo was just waiting for Dean to flip on the radio and use the music to drown her out - that was his usual avoidance strategy. He hadn’t yet - which confused her.

“You think Gabe’s gonna give me a ton of shit?” Dean’s voice was pitched a bit lower than usual, as though he were nervous.

“Shit because he _likes_ you. Not shit-shit.”

“How eloquent.”

“I’m a poet, what can I say.”

“Put that on your damn résumé.”

**Notes for the Chapter:**

> Every time I attempt to estimate the total number of chapters… it’s doomed to grow waaay beyond that. So, even if this was initially going to be a total of five chapters, I lied. Because of reasons.


	5. Chapter 5

After hitting some unavoidable traffic because of a ridiculous amount of construction near the airport, Jo and Dean finally rolled up to the arrival gates and looked around for Gabriel. Dean made a mental note that he most _definitely_ needed to head out early tomorrow morning to pick up Cas, because that construction mixed with rush hour? It wasn’t gonna be pretty.

“Was it Delta?” Jo’s eyes were flickering to the gate numbers and arrival labels as they drove slowly along the curb. “Or US Airways?”

“Doesn’t matter, I just spotted a tacky-ass leopard print suitcase,” Dean groaned and spun the wheel to park. “And, yep. There’s Gabe.”

The man sauntered over to the car (complete with matching luggage set) and flashed a grin while Jo was opening the door. “Heya my virgin in white! You excited for your big day? Dean, be a doll and get my bags.”

He wrapped her in a hug while the other man rolled his eyes and popped the trunk of the car. Although he _had_ been trying to behave around Anna, Gabriel was a _completely_ different story. So he didn’t hesitate slamming the bags into the trunk unnecessarily rough just to hear the man shriek, “Be nice, you _barbarian_!”

Jo giggled and let Gabe spin her around before answering, “Well duh, wait til you see my dress! Oh, and I guess I like my fiance, or whatever. So glad you could fly out and make it, it’s great to see you!”

“Anything for the princess,” he smacked a sloppy kiss to her cheek before spinning on his heels and turning to Dean. “And how’s my _other_ princess?”

“Not too bad, Dopey. When did you become a fashionista dwarf?” Dean gestured to the appalling bags before he shut the trunk.

“A birthday gift gone wrong, of course. Waste not, want not.” He clapped Dean on the back, “And I may as well be your goddamn Fairy God Mother, I’ve heard Anna’s been being a wicked bitch.”

“Hah!” Jo tossed her head back with a very unladylike snort. “Oh. Sorry. How’d you hear about that?”

“Angry texts from the sissy,” Gabriel waved his phone, “I could quote ‘ _Dean is too busy drinking and neglecting his duties right now, so he may be late_ ’ and _‘I’m appalled by his table manners,_ ’ oh cry me a fuckin’ river, Anna needs to pull on her big girl panties.”

Dean stared and blinked.

All right, he saw Anna bitching to Gabe from a mile away. But, fuck, this was what he was hoping to _avoid_. What if she had been sending all these things to _Cas,_ too? What if he had his sister telling him the guy he was sort-of-talking-to was a disgusting, alcoholic slob that didn’t care about the rest of his family and just wanted to get laid or some shit? Fuck, fuck, fuck.

But… it sounded like Gabe was kind of _defending_ him, right? Or at least telling Anna to get off her high horse... that was something, right?

“Don’t pull something from thinking too hard, even though I _know_ that‘s rough for you,” the man teased and walked around to pull open the back door to the Impala. “I told Anna to chase some tequila with a xanax and she was being a spaz. That’s just how she gets when family is involved.”

Still, Dean was gulping all over again as he got back into the car, “I don’t get why she hates me all of a sudden.”

“Eh,” Gabe got comfortable in the back seat as Jo turned around to listen to him. “She’s always been hella protective over Cassie. Who the hell knows why, he’s a big boy. She’ll get over it, she just hasn’t gotten the gross-love-struck drunk texts _I’ve_ gotten from you to know that your intentions are pure.”

“ _Pure_ ,” Jo repeated. “I don’t think I’ve _ever_ heard _anyone_ refer to Dean’s ‘intentions being pure’ before in my _life_.”

“Oo, then I should read some texts to the class!”

“Stop that shit right the fuck now!” Dean snapped, “If you pull out that phone, the next place it’s going is up yer ass!”

“See, now if Anna saw _this_ charming side of him, all would be forgiven,” Jo rolled her eyes and punched the man in the shoulder as he pulled away from the curb. “So Gabe, can the Fairy God Mother help Dean win over the Prince’s heart and destroy the evil witch?”

“I said bitch,” Gabe wiggled his eyebrows, “And, duh. I’m fuckin’ magic. Sooo back to this lovely Roadhouse I‘ve heard so much about? I‘d rather have a beer and see some of the ladies before heading to my hotel, if ya don‘t mind.”

Dean groaned loud and annoyed, “I’m sure the party will still be going strong. Just keep Anna away from me.”

A smirk tugged across Gabe’s face, “Oh, don’t you worry. You’ll get your ‘happy ending.’”

“Gross.”

\---------------

The party was in full swing when they got back, Ruby and Meg greeted them with a round of drinks when Jo shot them a text they were on their way back to the group.

Gabe nuzzled Meg’s face, and thanked her a thousand times for the beautiful ( _disgusting_ , sugary) concoction she placed in his hand, while the other two clinked their beers together. Gabe quickly disappeared through the somewhat-crowded get together to find his sister. To which, Dean was thankful. At least if Gabe was dealing with her, _he_ didn’t have to. Jo elbowed him in the side with a knowing smirk.

“What?”

“Gabe really _does_ like you, ya know.”

“Yeah, he only made me cry twice on the car ride home, so that’s good.”

“Shut up, you know he’s got your back. That’s all I’m saying,” she took another sip from her beer. “I’m _also_ saying you shouldn’t get mad that he just grabbed Sam’s ass.”

“What?!” Dean spun around to see his brother was, _indeed_ , bright red and looking around the group wildly while Gabe was two people over smirking proudly to himself.

“Yep. That just happened.”

“He’s such a little shit.”

But he had to admit… Sam _did_ look hilarious as flustered as he currently was.

So Dean wasn’t mad at all. He couldn’t quite grasp _how_ his Cas was related to these two ridiculously different (crazy assholes) people though… woah, _his_ Cas? Where had _that_ come from?! He needed to _chill the fuck out_ right there.

“I need another drink.”

\-------

Dean honestly thought the bachelorette and bachelor parties were the last times he would need an iron stomach to get through the night alive. Unfortunately, having a group this big together for a celebration (filled to the brim with border-line alcoholics) had beer after shot after beer being pushed into his hand, and he couldn’t exactly say no, right? _Especially_ since it was the _damn bride_ who was pouring all the booze.

“Isn’t gonna be fun when we’re all hung-over tomorrow, Joanna!” Dean tried to sound angry, but he giggled instead as he toasted with the surrounding group (composed of Meg, Ruby, Sam, Lisa, Gabriel and a _thankfully_ drunk and fun Hannah).

“Hair of the dog?” Lisa suggested, “Bloody Mary's for breakfast, and then we won’t feel a thing!”

“I can’t wait to see your drunk asses stumble down the aisle,” Gabriel laughed, swishing his drink around in his cup. “Who ever bites it first owes me a lap dance during the reception as punishment.” He swung his gaze around to who he had _happily_ focused his harassment on the majority of the night, “Although I expect one from the moose no matter if he takes a tumble or not.”

“I’d _pay_ to see that,” Ruby snickered, “If he lost his balance and fell over, you’d be a fuckin’ _pancake_.”

“I’d die a happy pancake,” Gabe winked, “I’d take the lap dance tonight, if you’re up to it. Got the room allll to myself, since Cassie’s flight was delayed.”

“Oh my god,” Sam covered his face with his free hand not holding his beer. “How do you put up with him, Dean?! You have to break up with Cas, this short-stack isn’t allowed to be a brother-in-law. Cancel his flight. Kill his goldfish. Do _anything_.”

Dean choked on a sip of beer then started laughing, “I may just propose to Cas tomorrow, to keep short-stack around for _your_ benefit.”

“Please and thanks!” Gabriel finished his drink, set it on the table, and without hesitation plucked Sam’s beer from his hand and chugged it as well. “Or we can just elope tonight, Sammy. Would you be mad, Jo?”

The blonde snickered and shook her head, “Not at all. In fact, I encourage it!”

“You guys!” Sam was blushing a new shade of bright red as he snatched his beer back from Gabriel’s clutches.

“You need another?” Meg patted the empty-handed man on the cheek, who quickly nodded, and then she disappeared.

“I wanna daaaance!” Hannah announced loudly, looking around the room. “Why isn’t anyone dancing?”

Ruby grabbed a hold of the woman’s hand and tugged, “Oh, drunk Hannah, how I’ve missed you! Let’s hijack the jukebox and get this party started! Any requests?” She looked around the group as she led a giddy, skipping Hannah along the route.

“Nothing shitty!” Dean responded, at the same time Gabriel yelled, “Kanye!” and Lisa said, “Miley!” Then Dean cried out in indignation, “That’s _all_ shitty! You‘re all _not_ my friends anymore, starting _now_!”

Meg brought Gabriel a drink, along with a straight-up tray full of beers to make sure she ‘didn’t have to make a run anytime soon,’ which Dean was grateful for. He’d reached the foam at the bottom that tasted like piss and eagerly swapped it out for a cold one. Sam needed a new one as well, since Gabriel had taken it upon himself to ‘help him’ drink his last. Rude.

The jukebox was fired up, and some random pop song with a good beat (Dean wasn’t about to admit that) started blasting, and he found himself tapping his foot along. He was surprised, as Hannah and Ruby shoved aside tables to create a little dance floor, at the number of people who joined in. Most of the girls he knew enjoyed dancing, and Garth never turned down the chance, but when Benny and Zeke joined in, Dean started laughing. And then Gabriel pulled a kicking and screaming Sam onto the dance floor.

The only thing that could make this night better was if _Cas_ was there.

Did Cas dance?

Would Cas like this crazy group of friends he considered to be his _family_?

He had so many questions, and his drunk brain was playing through scenarios as he idly sipped his beer and watched Hannah start a goddamn conga line.

When was Cas headed back to New York? Or California? Or wherever the hell he was next? Was Dean even going to get more than one night with him? At least one night was better than they had last time, but Dean was _greedy_ and wanted _more_. Cas had to too, _right_? Wanted more? He’d agreed to be his fucking _date_ to a fucking _wedding_ , it’s not like it was a 2am booty call, it was a flight across half the US to get here, and meet friends and family. It was the kind of we’ve-been-dating-for-months event you’d invite a serious significant other to. But… _ugh_.

He shook his head as Lisa, on the end of the conga line slapped his rear in a loop around the bar. He smiled to himself, because the positive energy in the room was infectious - even _if_ he was second guessing himself and being stupid. He didn’t have to think about these things now, they were celebrating for fuck’s sake!

Which was why he snagged Meg and Jo for another round of shots at the bar, and challenged Charlie to a round of pool.

Tomorrow was the day he’d be able to figure it all out.

Tonight, he was supposed to have fun.

\---------

Dean’s alarm went off _way_ too early for how _late_ he’d stayed out. He’d gotten drunk as a skunk by midnight, but spent the rest of the night chugging water, munching on snacks and sobering up. He hadn’t dared driving Baby even a _touch_ buzzed, but Sam had been good to take him and the Impala home. He was pretty sure his brother got a cab after, or something about catching a ride with Kevin or whatever, but the _point is_ he was fucking exhausted, but not _hung over_. There _was_ a God.

Then, he got a new rush of energy, because his alarm meant _get the fuck up you get to see Cas_.

Halle-fucking-lujah!

He’d set it just early enough to be able to hop in the shower, shave and make himself look as appealing as humanly possible before picking the other man up. He also figured in time for driving through a Starbucks and picking them up coffee. What did Cas like though? Whatever. Coffee was coffee, and it was the thought that counted, right?

He hoped.

He’d taken all of his wedding shit to the venue the day before, so all he really had to do was show up, which was nice. There were still random errands to run (something that had to do with boutonnieres, but Benny hadn’t mentioned if that fell on him yet) so now he was pulling on his jacket and hopping in the car.

There hadn’t been any texts sent from the man earlier that morning, so he assumed there hadn’t been anymore delays. But Dean got on the website just to double check. As he thought, everything was a-okay and on time - so he sent a text to Cas, to let him know he was on his way.

It was a chilly morning, and the car took an _obnoxiously_ long time to heat up. Still - he had his stupid stomach doing _flips_ and _butterflies_ to keep him warm and fuzzy, none-the-less. _Shit_ , he was being a little girl. He was at a stop light, a few minutes away when he finally got a text from Cas, confirming the plane had landed and they were unloading now. His timing was spot-on. By the time Cas hit up the baggage claim, and he’d looped through the airport, they’d be meeting up at the perfect time.

Dean _prayed_ this was a sign that everything was going to work out. Hell, he may have even melodramatically crossed himself, then slapped each of his cheeks once.

And, _shit_ , the little old lady in the car next to him was blatantly _staring_ and _sneering_ at him.

Whatever.

She was just jealous she wasn’t on her way to pick up a blue-eyed sex god.

Fuck her.

And her little old lady Buick.

Dean rolled his eyes when the light turned green... what was his issue? Picking a mental _fight_ with a _grandma_?

Oh, _hell no_! Said grandma just _cut him off_! She was gonna--

Stop, _stop_ , he _had_ to calm himself down. This was the final countdown, he’d be with Cas in no time and that was good... _that was very good_. He just needed to make it to the airport in one piece. No need to get dramatic about anything now. Dean tried to find his zen place and coasted easily through the rest of the way, keeping that in mind.

Once he was parked along the curb, Cas asked him what kind of car he had, to which he responded, ‘The perfect kind.’

There was a little ‘…’ hovering over where Castiel’s next text was going to pop up, but that’s when Dean saw him with his head down typing on his phone while walking along the sidewalk. So Dean wasted no time, hoping out of the driver's seat.

“Hey good lookin’, need a ride?” He whistled and cat-called over.

Castiel’s eyes widened as he looked up and froze in his spot, before a grin spread over his face and he purposefully changed his direction towards Dean and the car.

Dean walked around the Impala and met the man on the sidewalk and didn’t know what to do first.

Did he hug him? Take his bag? Kiss him? Shove him in the back seat for a quickie?

“Damn, I missed you,” he breathed out once they were close enough and cursed when he realized his _thoughts_ had left his fucking _mouth_. “I mean, oh hey. How was your flight?”

“Hello, Dean,” Cas dropped his bag with an impish smirk and closed the distance between them completely.

And Dean meant _completely_.

His lips were brushing against Cas’, the man’s tongue lapping against his slack lips which Dean eagerly responded to. Dean’s brain goes on autopilot, needing to be _closer_ , and wraps one arm around Cas’ waist, while bringing the other to cup the side of his face. It just feels so natural, _so_ fucking _right_ , and when Cas nips his lower lip and _sucks_ he can’t help but moan.

Shit, shit, shit, now he really _does_ wanna throw him in the back seat for a quickie.

Before things get _too_ heated (although Dean is now friggen effectively riled up and rearing to go) Cas pulls away and smiles with bright eyes. “The flight was fine. Couldn’t wait for it to land, of course. I’ve been wanting to do that for quite a while,” Cas’ voice is a bit deeper and tinged with lust as he rubs his thumb across Dean’s jaw. “And more, of course. But this isn’t the ideal location.”

“U-uh, yeah,” Dean cleared his throat and gestures to the bags, haphazardly forgotten on the ground. “Wanna load up and get out of here?”

“I’d like that very much,” Cas reaches down while the other man opens the rear door for him to toss back the luggage.

“I got coffee for you. Know you were up at the ass crack of dawn and all,” he’s trying to make his voice confident, he _really_ is, but Cas is so fucking good at taking his breath away, it’s _unfair_.

But it makes Castiel _glow_  - so it’s all worth it.

After dropping his bags and shutting the door, they both climb into the car and Dean starts her up. Cas reaches for the coffee and takes a sip while they pull out and hums in satisfaction.

“Thank you for this,” he reaches across and squeezes Dean’s thigh, which has the man blushing despite himself.

“So where we headed?” He asks immediately once he merges back onto the main road.

“That’s where I have a conundrum,” Cas frowns out into traffic and sighs, “I was _supposed_ to be staying with Gabriel, but I received a text last night saying he _got lucky_ , so I’m not welcome in the hotel until he gives me the all clear. Needless to say, I haven’t gotten the 'all clear' yet.”

“He _scored_?!” Dean demands, whipping his head around to Cas. “With _who_?! He was hanging out with me and the bridal party all night! What the hell!”

“He’s choosing to keep that a secret,” Castiel shrugs and continues, “I’ve been trying to get in touch with Anna to see where she’s staying but I’m guessing she’s still asleep. So even though Gabriel will be upset, I need to shower and get the airport filth off me so I figure I’ll just show up and hope they’re not going for round two. Or three. Who knows.”

“Dude, you can shower and get ready at my place,” Dean states as casually as humanly possible. “I don’t have to be to the venue for another hour or so. Whoever Gabriel _tricked_ into going home with him will have to be back by then too, so I can drop you off on the way?”

“I don’t want to be an inconvenience-” Cas said almost _too_ quickly, which had Dean raising an eyebrow.

“If it was a problem, I’d let you barge in on Gabe. Cas, it’s _fine_. I _asked_ you to come out, I _want_ you here, hell,” Dean shifted a little uncomfortably, “If you wanted to stay with me the whole time, I’d like _that_ too…”

When Dean dared to glance back over, Cas was wearing a strange smile, and nodded.

“All right. That’d be great, then.” He squeezed Dean’s thigh again and let his finger tips brush against the denim. “Would you be opposed to joining me?”

Dean may or may not have swerved in his lane a little.

“Hell no.” He laughed nervously to cover up his excitement then winked. “That’s actually a rule. You use my shower, I’ve gotta be there to supervise.”

Wearing a smirk of his own, Cas countered, “Oh? Is that a rule you implement with all your guests?”

“Nah. Just something I came up with today.”

“Just drive, Dean.”

“Roger that.”

\-----------

Dean couldn’t be happier with this turn of events. He was worried he’d be dropping Cas off at the hotel, then stewing in sexual tension until he saw the man again at the wedding. But, _nope_ , today was turning out much, _much_ better than he could have anticipated, and he was currently peeling off Cas’ jeans - blindly - from where he was pinned against his bathroom wall while the water heated up.

Castiel was fucking _efficient_ and already had him _buck ass naked_ and _needy_ from a few hot kisses in the entry way, and then a chase (complete with undressing) to the bathroom. He whimpered into the man’s mouth as Cas tugged on his hair, and finally gripped the waist of his pants to pull them off. His boxers were being stubborn and still hanging, on which Dean did _not_ like _one bit_. He _needed_ to get Cas naked. _Needed_ to see the man and touch his bare skin.

There was a fog slowly creeping into the humid room, that told them both the temperature was nice and ready. Cas broke away from him just long enough to shove down his own boxers then lead them both into the shower. Dean didn’t hesitate to openly gawk (and maybe drool a little) at Cas’ _delicious_ ass while he was stepping out in front of him.

“Dean-” the low lust-wrecked voice snapped him out of his reverie and had him moving so fast he was lucky he didn’t trip and break his neck.

The spray of water alarmed him when he finally followed Cas in, but not as much as getting _shoved_ against the tiled wall and having the wind _knocked_ out of him.

Cas _wasn’t_ fucking around.

And Dean didn’t mind in the _slightest_.

He was practically purring as Cas pressed his body flush against him, and went to work nipping and sucking at his neck. It was frantic and rushed - not in the way that they were on a time constraint, but in the way they needed each other _now_.

Dean thought, _maybe_ , his drunken mind had blown his previous experience with Cas out of proportion but now sober-Dean knew that was huge  _lie_.

Speaking of _huge_ , his expectations and memories did _nothing_ to honor the size of Cas’ cock, now that it was leaking, hard and rutting up against him. Fuck, this man was so hot. His hands were clenching Dean’s hips, holding him against the wall with a ridiculous amount of strength to the point Dean _couldn’t_ move even if he _wanted_ to.

But, nope, he was _quite_ happy right here.

It was amazing - how _easy_ it was to give up control to Cas. Let him hold him down, have his way, get as rough as he wanted and leave marks. Dean could feel the bite of his nails digging into the meat of his own hips as he tried to thrust against Castiel and find _friction_. He moaned as Cas gave him some leeway, his mouth returning to kiss Dean’s swollen lips while one of his hands dragged along the shower-slick skin of Dean's stomach.

Dean was panting, and wrapped his arms around Cas’ back to keep from falling over - plus, he wanted to grab onto _something_ he could use as _leverage_. His hips were arching wildly, their erections trapped between their bodies and Dean begged into Cas’ ear, “You gonna fuck me, babe?”

Cas drew Dean’s earlobe into his mouth and tugged. Once Dean shivered and moaned against him, he drew away and shook his head. One of his hands reached up to cup Dean’s face to make sure he was looking him _right_ in the eyes while he flicked his tongue lewdly into Dean’s open mouth.

“Not now, we’ll save that for _tonight_. I want to have all the time in the world to take you apart, not just an hour,” he smirked. “I plan on fucking you until you can’t walk for a week, and you have obligations today... so we’ll wait.”

Dean huffed and felt both a tinge of disappointment, and another wash of arousal before taunting, “Saving it for the wedding night, huh?”

“Of course,” Cas pulled him off the wall enough to snake one hand around to Dean’s ass. He gripped the flesh and spread his cheek wide enough to drag his finger over Dean’s wet hole. “I _am_ a gentleman, after all.”

“Fuck, _Cas_ ,” Dean fell forward into the man’s arms and arched his back wantonly into the touch. “You’re _not_ a gentleman, you’re a goddamn _tease_.”

“Oh?” He raised an eyebrow and circled his finger around Dean’s entrance while he dropped the other hand, cupping his face, downward. “I don’t consider _this_ teasing-”

He lowered his free hand even _further_ and wrapped both their cocks in his grip. Dean moaned and bucked into the touch, while Cas added more pressure with his single digit, _barely_ dipping into Dean’s ass. Dean’s arms grappled desperately at Cas’ shoulders, while the man began pumping both their cock’s together in a firm and steady rhythm.

He was falling apart by the _second_.

Even _more so_ when Cas started fuckin'  _kissing_ him again.

It was so _intense_ \- a different kind of passionate, and Dean’s body was on _fire_.

He didn’t know _where_ to concentration, there were _too many_ sensations, he was being pulled in too many _directions_ \- the fervor and power Cas’ tongue was _devouring_ him with - the quickening, deliberate _friction_ of Cas’ hand on their dicks - the twisting of his finger that was now all the way  _inside_ him. Fuck, _where_ had this man come from?!

Dean couldn’t do much but hold on and try to kiss him back with equal ferocity for as long as he could. But fuck, the fire inside him was coming to a head, and he _knew_ he was chanting Cas’ name into the man’s mouth. He could feel him _smiling_. For a while, he’d tried (really _really_ hard) to keep the rhythm of his hips in time with Cas’ hand, but now he was jerking erratically and it was all going to hell.

He was falling apart, panting and pulling his head away to bury his face against Cas’ neck. His orgasm poured over his body like a fucking _tsunami_ , and he biting down against the man's flesh while his moans echoed throughout the shower.

Cas was gasping too, and Dean could feel the hot stick of cum on him while he was fighting to stand upright.

Castiel slowly moved his hands to wrap around Dean’s shoulder blades and hold him close, maybe to keep himself up, as well. His kisses turned lazy, but he didn’t stop. Just kept pressing them to Dean’s forehead, his cheek, and when Dean finally shifted up, his lips.

And, yeah, Dean kind of nuzzled him. Whatever. He _felt_ like it, so he _did_.

“I’ll be jealous if this is a new rule you hold all your guests to from now on,” Cas teased in between tender kisses.

“You’ll just have to be my guest more often,” Dean teased back and reached for the soap. “Fuck, you’re awesome.”

Cas’ chuckles echoed through the bathroom as he rubbed circles along Dean’s back. “I can’t wait until tonight. That will be even more ‘awesome.’ No offense to Joanna, but I hope to get back here as soon as socially acceptable. I want as much time with you as possible.”

Dean felt the color drain from him face. “Uh, _yeah_. About that…”

So Dean let Cas wash his hair for the second time that day, as he grudgingly relayed the story of Jo and her annoying ‘point system’ and the bet that he would duck out of the wedding, first chance he got, to be with Cas. It was even _more_ painful to admit that Dean had arrogantly proclaimed - out of pride - he’d be able to make it through the whole damn thing. Cas was strangely silent, as the man bitched and moaned about how stupid he had been.

Once he had finished, it was quiet for a second before Cas merely acknowledged everything with a, “Hmm.”

“ _Hmm_?” Dean spun around and stared, because that _wasn’t_ what he had been expecting.

He had been expecting to be called an _idiot_ , and interrogated as to _why_ he’d done something as _dumb_ as that.

“My bet is the same as the ladies.” Cas smirked. “There is _no way_ you’ll be able to last the night.”

“Huh?” Dean’s eyes widened. “ _Wait_ , you’re not on _my_ side?!”

“Not at all,” his smirk widened. “I happen to enjoy being on the _winning_ side. And the winning side implies that there’s no way in hell you’re staying for the duration of the reception.”

Dean felt his blood freeze, even under the hot water beating down against his back. “ _Excuse_ me?”

“You’ll be begging to go home with me well before the ending, Dean,” Cas leaned towards him. “Because _all_ you’ll be able to think about is how I’m going to bend you over and fuck you harder than you’ve been fucked in your _life_. You’ll be a whimpering _mess_ after I make you cum over and _over_ again,” he paused thoughtfully, “Why would you want to stay for longer than you have to, when we have an entire night of _that_ ahead of us, back here?”

Cas turned the nozzle to the shower off, and Dean’s cock twitched with a new wave of arousal.

The blue eyed ( _fucking devil_ ) man shrugged and stepped out of the shower to grab the towel hanging outside while Dean stood there, dumbfounded. _Hell no_. He _didn’t_ … oh, he totally _had_. The fucking _asshole_.

Dean tore back the curtain, with a look of determination on his face (disregarding the full-frontal nudity) and growled, “It’s _on_ , fucker!”

Castiel didn’t respond in words, but with a _look_. And that _look_ told Dean, no matter _how much_ bravado he was showing, he was _fucked_. Totally and royally _fucked_.

**Notes for the Chapter:**

> I always tell myself I'll wait longer between updates, but I have no self control! Oh, hey, Cas is back :)


	6. Chapter 6

While Dean was pulling on his abandon clothes (he had to follow them through the halls like a trail of goddamn bread crumbs) he attempted to smash down the irritation tingling in his body. It didn’t help that Cas was _humming_.

_Fucking humming_ happily to himself as he dug through his travel bag.

“Remind me _why_ I invited you again?” Dean groused when he finally found the last article of clothing - his shirt - and stomped back over to Cas. “You’re kinda a pain in the ass.”

Cas slowly stood up to his full height (which _happened_ to be barely shorter than Dean, but _damn_ did he seem _taller_ ) and tilted his head to the side. With that dumb, self-satisfied smirk. “And yet, you can’t seem to get enough.”

“Yeah, yeah,” he couldn’t help it, he couldn’t keep his distance when Cas was finally _right fucking here_.

So he walked up to him and wrapped his arm around his waist, and kissed the barely-there stubble along his jaw. It was as though _gravity_ was pulling them together, and who was Dean to deny fuckin’ _science_? Duh.

Considering how cocky and arrogant Castiel had been before, he responded to the touches with affection, and fondness - massaging his fingers into the tight muscles of Dean’s back and kissing his forehead. He found himself moaning, despite his best efforts and _melting_ into the touch. However, his own pride reared its head no matter how much he was loving the current (and random) adorable doting. So, _obviously_ , he had to ruin it.

“Calm before the storm, Cas? Luring me into a false sense of security?”

Apparently, Cas didn’t fall for it.

He pulled the man closer and rubbed his shoulders, while Dean moaned and lulled his head into the crook of Cas’ neck. He never wanted this moment to end, dammit.

So, naturally, when Cas’ phone buzzed, the moment was over.

The noise Dean made borderlines on a growl, which had Castiel raising a _very_ interested eyebrow. But instead of commenting on _that_ , he said instead, “Gabriel informs me the coast is clear and we can swap hostages.”

“As much as I don’t want to let you go,” Dean shifted his body enough to slide his hands into Cas’ back pockets and brush their noses together. “I cannot _wait_ to see who I’m gonna harass for going home with _Gabriel_.”

Cas flashed him a crooked grin, “Myself, as well.”

\-------------

Like any gentleman would, Dean walked Cas through the lobby, helped with his bags (even though Cas protested, a bit annoyed _he could handle them himself, thank you very much_ ) and lead them to the hotel room door. He kinda regretted his decision, too. Cas didn’t have a roll-y bag and his shit was _heavy_ as hell ( _you can never have enough books and shoes, Dean_ \- Cas had told him) ( _You’re so gay_ \- Dean responded back) ( _you’re saying you don’t like my dick in your_ -) ( _enough_!).

Anyways!

They were standing in front of the door and Dean wanted to do the honors of knocking.

Gabriel swung open the door, wearing one of the complimentary hotel robes and wiggling his eye brows at both Dean and Cas, immediately asking, “Please tell me you took advantage and had an early morning fuck-fest?”

“Must you be so crass,” Cas narrowed his eyes. “Now, if you’ve _forgotten_ , Dean and whoever you conned into intercourse last night have a wedding to attend to - so they should really be on their way.”

“You are nooo fun at all, little brother!”

Dean found himself smiling as he watched the two banter back and forth. Yeah, he thought _originally_ they were night-and-day different, but they had the same kind of bite, the same kind of sass that you’d expect from two people in the same family. It was kinda cute. It was funny to see it in action, because _this_ was the type of thing _everyone_ said that Sam and himself had-

“Sam?!” Dean squealed, and his jaw dropped as the man tried to ‘sneak’ out of the room from behind Gabriel.

Because, of course this fucking _Sasquatch giant_ could really _sneak_ out of _anything_ , towering over the little muckrake who had _apparently_ _taken his brother home_ last night?!

“Are you _kidding me?_!” Dean whipped around to look at Cas, who was shrugging at him.

Dean was about to say something to Cas, but then noticed something _else_.

He watched Cas’ expression go from an indifferent ‘ _what-do-you-expect_ ’ to ‘ _what-the-fuck_ ’ in the blink of an eye, as he squeaked, just as awkwardly as Dean had, “Jessica?!”

He whipped his head around so quick, he was surprised he didn’t get fucking whiplash and saw, yeah, there was a mass of curly, wild, blonde _fucking sex hair_ walking out behind Sam.

She smiled and waved, while Sam looked absolutely _mortified_ at being caught by his brother.

Gabriel winked and casually commented, “Oh, I couldn’t decide if I wanted a bridesmaid or a groomsman, so I took home _both_ ,” he smacked their rears, “Now go frolic, I’ll see you hotties at the wedding.”

Jessica rolled her eyes and turned around to give Gabe a quick kiss on the cheek to say goodbye as Sam marched silently and stone-faced ahead. Gabe whispered something in the blonde’s ear, that had her tossing her head back and laughing, then she finished with a nod.

Dean had been speechless the entire time.

He couldn’t move.

He needed a lobotomy. Or _something_ to _scramble_ his memory.

“So good to see you, Cas! We’ll catch up soon, all right?” Jess gave Cas a quick hug before calling to Dean, “Meet ya at the car!” and chasing down Sam who was, no doubt, wandering aimlessly around the halls, just trying to get away from that awkward situation.

Dean _finally_ cleared his throat and turned to Castiel, “Uhh… so… that was my brother? We’ll try for another introduction after he finds his brain and walks it off.”

“Yeah, I _may_ have fucked those out last night,” Gabe shrugs and pats Dean on the back. “I _like him_.”

“I. Cannot. Deal. With. You.” He abruptly turned his back, effectively blocking him out completely and kissed Cas quick. “I’ll… see you at the wedding? Can you please kick your brother in the balls for me, or something?”

Cas couldn’t stop smirking, “I believe this is all _much_ too amazing to stop him, he’s on a roll, Dean.” The man leans in and nips Dean’s earlobe, “Besides, you’ll have _other things_ to worry about, when we see each other again.”

“Oh god. I forgot about that.” Dean cursed and wanted to slam his head into a wall. “How did this day fall apart so fucking fast?!”

“It hasn’t,” Cas reassured him, “Now, go. I think you have some harassing to do.”

“Bye, Deano!” Gabe called from behind him.

“I’ll see you later, Cas,” Dean muttered through grit teeth, and kissed the man once more. “Gabe, you’re dead to me.”

“Lies, I’m practically part of the family! Or at least _in_ the family…”

“Over my dead body!” Dean shouted over his shoulder, as he stomped away.

\-----------

Dean continued his stomp out to the parking lot to see Jessica and Sam waiting by the Impala. It was always easy enough to find, and the two were currently locked in a stare down, Dean was unable to see his brother’s face but Jess wore a shit-eating grin. Dean huffed as he finished the trek to his Baby and unlocked the doors. Strangely enough, Sam made his way to the back seat with his tail between his legs. Jess rode shotgun like a _ray_ of fucking _sunshine_.

There was a tension in the car, and Dean had no idea what to say. Was he supposed to be saying anything? Were they waiting on him? What were they expecting?

Jess was finally the one to break the silence.

“So did you have a good morning, now that you’ve been reunited with Mr. Dreamy?” She cooed, leaning closer to Dean as he started the car.

Okay, _that_ was something Dean could handle.

“Yeah,” he found himself smiling like an idiot thinking about Cas. But then he frowned. “Although, Cas seems to agree with the peanut gallery and thinks I’m not gonna be able to keep my hands to myself at the wedding. He’s pretty fuckin’ sure of himself, ain’t he?”

“Well, you _do_ look at him like you want to _eat_ him.”

“Hey!” He snapped, but all right, so sue him, he usually _did_. “Nice introduction, by the way, Sammy. Cas probably thinks you’re an easy, kinky sonuva bitch now.”

Sam didn’t respond in words, but with a, “Unnghh.”

“You weren’t even _drunk_ , dude, you _drove me home_! What the fucking hell?!”

“Don’t. Dean. We’re pretending this didn’t happen.”

“On _what planet_?!” Dean demanded, shooting him a glance in the rear view mirror. “You acted like you _hated_ Gabriel last night! You trying to tell me that this was some mad sexual tension, or something?! And you, Miss Moore!” He couldn’t help but laugh, “You are a _harlot_!”

She shrugged and grinned, “What can I say, apparently you don’t know me that well,” she winked, “I may be a nice Midwestern girl but I know a good time when I see it. And let me tell you, Sam-”

“Jess!” He snapped, glowing a bright red color.

“What?” She raised a challenging eyebrow. “Yeah, it sucks your big bro was the one to pick you up, but don’t even try to _pretend_ you didn’t have fun.”

“Don’t you dare tell anyone!” Sam’s voice was pleading with both of them, “Please. I… don’t know.”

“Yeah, yeah, Sam.” Dean snorted out loud, “Cas was right… this is teasing material for the next century!”

“I hate you. I hate everyone.”

“Cheer up, buttercup,” Jess reached around and gave his knee a good, hard smack. “We’ve got a wedding to go to!”

\--------

When they arrived at the venue, everything was _chaos_.

Dean had no idea if this was normal or not, considering he’d never been in a wedding before, but it didn’t _look_ like it was. All the groomsmen were running around like chicken’s with their heads cut off, while Becky and Hannah barked orders about setting up the tables with the flowers and hanging yards and yards of fabric along the tables for decoration. Becky had a false eyelash that had fallen off sticking to her cheek and Hannah’s hair was half curled as she tried to fluff all the arrangements _just so_.

Jess excused herself to run and start work on getting herself ready where the other bridesmaids were, and the brothers were immediately on edge.

Zeke and Victor looked like they had been called in at work to deal with a _sniper_ , all cold sweat and wide eyes as they tied bows with shaking hands and coiled rows of baby’s breath. Dean would have laughed, but Becky was charging _right for them._

“Dean!” Her expression softened when she cooed out, “ _Sam_ …” but then seemed to snap back into military-mode. “We need you to bring out all the chairs and set up the aisles! _Now_!”

“Jesus Christ! There are _hours_ before the fuckin’ wedding! Chill!”

“Don’t take the Lord’s name in vain!” Someone shouted across the room.

“We need the Lord with us!” Another voice.

“He hath turned his back on all his children!!”

“Motherfuck, everyone’s so dramatic,” Dean groaned, and turned around to a _very_ serious Miss Rosen. “All right, now that the brawns are here, where are the friggen chairs?! And, uh, you’ve got an eyelash…”

\---------------

It was days like _this_ , Dean wished he were a woman.

Scratch that, not a woman.

But only had the _obligations_ of a woman.

Although, judging by the fog of aerosol coming from the room they were getting ready in, they’d all be high by the time they were done getting their up-dos, so maybe not. He’d settled on physical labor, and hauling thousands (okay, not _thousands_ , but between the four men, definitely _hundreds_ ) of chairs out into the ballroom. He was not looking forward to putting them all back. He was _also_ not happy about the fact that all he’d be handed this morning was a _damn mimosa_.

Where were the _real_ drinks?!

This wasn’t a freakin’ Sunday brunch, this was a -

Oh, yeah. It was a wedding.

So sue him, if he thought a bourbon would be a little bit more appropriate, but Benny had assured him once they put the room together there would be beer.

And the reception had an open bar.

_That_ was something he could get down with.

Half the bridesmaids were milling around, hair perfectly coiffed and makeup picture-perfect when they reminded him that (duh) pictures would be starting within the hour. And, shit, he needed to get dressed. He needed a shower after hauling all that shit around, but three before noon seemed like a little bit of over-kill. So he groaned and dragged Sam over to where their suits were and peels off the layers of their sticky clothing to get into their ’uniforms.’

Dean had to admit, as he unzipped the garment bag, they looked pretty damn snazzy. Thankfully, Jo wasn’t one of those girly-girls who beat their men into submission and demanded pink and white wedding colors. Nope, they had gone with neutrals. Chocolates, taupe, silvers and charcoals. With so many damn bridesmaids, and so many different personalities (although they wore the same _style_ dress) they were able to pick their own color as long as it was in the same palette. Which, apparently, _meant_ something, as he’d overheard Meg bitching, ‘Thank god my porcelain skin looks flawless in this instead of that god-awful champagne! We can’t all look Mexican like Lisa-’

He hadn’t known there were so many different words for ‘brown’ and ‘grey’ until then, either.

Fifty shades, his ass, there were _way_ more than that.

All the men’s suits were a rich khaki, the only thing that was the _exact_ same, because the guys didn’t give a shit.

Guys were _way_ cooler like that.

While they were changing, Dean couldn’t help but glance over and cackle.

“What?!” Sam demanded, his eyes narrowing in a bitch face.

“You look like you have chicken pox, dude. You’re _covered_ in hickeys!”

He flushed again and started dressing double-time. “We’re not talking about this, _remember_.”

“Sorry, I can’t _not_ comment on the fact that you look like you’ve got the _plague_!”

“Drop it, come on,” his bitch face turned to puppy eyes, which he _knew_ was a sure-fire way to get Dean off his back.

So Dean went back to work on buttoning up his shirt and looking back down to the three pieces he had left to put on. This thing has so many layers, it would be more bullet-proof than his Kevlar. Weddings were weird.

Charlie popped her head in, “We’re about ready to head out for pictures!” She sounded excited and bounced in her place before yelping, “Sam! Did you get feisty with a damn _vacuum_?!”

“Charlie!”

Dean smiled to himself, because now that Charlie had taken the bait, there was _no way_ Sam was getting away from that. He’d never hear the end of it now. Sucks to be Sammy.

\----------

His cheeks were sore.

The damn photographer had made sure of that.

It was nearly two hours of photos, and now he had to smile his way through the whole damn _wedding_ and _reception_ , too? This was ridiculous, he wasn’t getting paid like a damn actor, and he felt like he was a supporting role in a fucking rom-com, starring Joanna Beth and Benny. Wasn’t the groom not even supposed to see the bride until the wedding?!

Of course it was a little unconventional, Dean knew that. They didn’t seem to give a shit, because the ‘best lighting’ was now, and they wanted the wedding to be during the evening. Benny still looked happy as fuck to see Jo in the dress, and whispered in her ear repeatedly how _beautiful she looked_ , and as much as it should make Dean sick it was stupidly sweet and he couldn’t help being happy for them. All right, so round one was over, and now it was time for the actual thing.

And thank god!

They all went to the ‘backstage’ area, as the ballroom was open and guests began trickling in. They were finally able to crack open the booze, and get the _real_ party started. Apparently, they didn’t want anyone looking drunk and disorderly in the pictures, which Dean thought was a shame, because that destroyed the _authenticity_ of their friendships. Hopefully they’d get more than enough when the photographer stuck around for the wedding. Garth would be done-zo in no time.

Charlie was peeking out into the ballroom and turned back around with a wicked grin that Dean caught immediately.

“Damn, he looks even _better_ without my beer goggles on. How’s that _possible_?!” Charlie whistled over and then clucked her tongue. “Too bad I’ve got a girlfriend.”

“Hey!” Dean admonished, but couldn’t help it - now he _obviously_ needed to sneak a peek too.

He leaned over-top her from behind the door frame and caught sight of him immediately - not that it was too hard. In addition to having a sixth-Cas-sense, he was like a fuckin’ shining beacon of _gorgeous_ in his suit with his hair actual _styled_ , all confidence and grace while he was chatting with Ellen. Oh, _shit_. He was _definitely_ getting the third degree right now…

But Ellen was laughing with him, leaning in and smacking him _friendly_ on the arm. _Shit_.

“Did he just…?” Charlie said Dean’s thoughts aloud.

“Win the ‘Mama seal of approval?’ Fuck, it looks like it.”

“In record time! He’s a _keeper_!” Charlie stood up quickly and ended up _smacking_ the top of her head on Dean’s chin, “ _Ow_ , what the fuck, stop gawking!”

It was then that Cas could feel eyes on him, and turned to look around the room. His gaze finally landed on Dean and the asshole _winked_. And maybe (definitely) Dean got all _tingly_.

“Can’t. He’s too hot.”

“Shut up, Winchester. Come on, do a shot with me!” She tugged him back into the room. “T-minus fifteen! Yay, team!”

\-------

Although Dean would have picked some kind of classic rock to walk down the aisle to (not like he was planning on getting married anytime soon or he had thought about it or anything stupid like that) he didn’t hate _too much_ on Jo’s choice to play Lana Del Ray. The ceremony was kind of _perfect_. No one tripped (everyone had been ridiculously respectful, and waited until the promise of an ‘open bar’ after the wedding to get annihilated) and things went _really_ smooth. When Bobby walked Jo down, just as Dean had suspected, the tissues appeared in the spectator’s hands as well as Bobby’s.

Even if Dean had been _forced_ to smile during the photos, this was anything _but_.

This was _genuine_.

And, sue him, if he got a little misty during their vows.

People cried, people laughed, and soon there was a borderline inappropriate ‘you-may-kiss-the-bride’ moment which had the audience clapping and cat-calling. He was laughing and lit up, and the few times his eyes made their way to Cas, his date with smiling happily too.

Damn, Dean was stoked he invited him.

_Anna_ even smiled at Dean once, which was _saying something_ , since she hadn’t really talked to him the _entire_ event. Dean felt _no_ regrets about that - she still scared the crap out of him.

Dean also noted the small glances his brother was sneaking at Gabriel, who looked _pleased_ as fucking _punch_ while watching the whole thing, and whispering to Cas once in a while.

As the processional started playing and they walked back, two-by-two, this was when Dean knew his _real_ challenge started. And, shit, he was _not_ looking forward to it. If that filthy grin on Castiel’s face was foreshadowing to, at least. Dammit.

\--------

While Dean hadn’t been in any other weddings, he had _been_ to many, which was why he could appreciate how much this one _kicked ass_. The buffet food was awesome (of course it was gonna be, Ellen threw it all together) and the bridal party’s table was more of a ‘seat yourself’ rather than stiff name cards, girls segregated to one side, men on the other. Which why he happily parked his ass right between his brother and Charlie. He had managed to sneak a full-handed grope of Cas’ butt on the way in, but duty called, and he had to sit at the head table until the meal and toasts and speeches or whatever were done.

Which was good.

Because he needed to steel his nerves.

Plus, it was really fun to watch Charlie lean over him and grill his brother.

“Soooo who’s the lucky playmate, Samantha?” Charlie inquired, after chewing a mouthful of food. “Dean, do _you_ know?”

Instead of answering, Dean just kept shoving food into his mouth, enjoying the way Sam was shifting in his seat. He also was noticing the fact that Cas had gotten out of _his_ , and was currently walking up to the table. But rather than going to _him_ , he headed to _Jo and Benny_.

Yeah, so maybe he was disappointed when he shook _Benny’s_ hand, and kissed _Jo_ on the cheek after giving Dean those fucking sexy bedroom eyes and _then_ walking back to his table with nothing _but_ a smile. Jerk. So he jammed even more food into his mouth and decided to eat his feelings instead. Seemed like the best solution.

“Oo, are you getting the cold shoulder?” Charlie changed her harassment target over to him.

Great.

“His strategy sucks,” Dean grumbled to himself.

“Huh?” Sam finally piped up. “What’s this about strategy?”

“He’s playing hard to get. Not gonna work.”

“Oh, that game thing you guys have going,” Sam commented, leaning in, “My bet’s on after the dollar dance.”

“Dammit!” Dean hissed out, “Not a single one of you dumbfucks is on my side.”

“ _That’s_ just it,” Charlie snickered, “We’re _not_ dumbfucks. It’s all good, Dean, just make an announcement when you give up. Some of us have turned our _point_ bets into _money_ bets, and I have some dough to collect, just saying.”

There was the sound of glasses clinking, Jo and Benny kissing, and the three downing the rest of their drink. Then, Dean went back to _savagely_ attacking his dinner. Charlie mumbled something about not choking, but he ignored her. He’d choke if he wanted. At least then, he’d get out of this stupid deal.

\----------

Soon, the buffet was cleared away, the tables bused and the lights dimmed down while the DJ set up the music. The obligations (besides the necessary dances, which could easily be accomplished drunk) were over and done with and the bridal party dispersed. Half went out to mingle, half went to get in line to the bar immediately. Dean was first in line with his brother in tow.

They both did a shot, and grabbed a mixed drink after tipping the bartender and lingered right around there.

“You’ve been weird.” Dean finally said it and poked Sam in the side.

“ _You’re_ weird.”

“I have a reason to be weird! I’m preparing for battle. You, on the other hand, had a walk of shame and should be over it.”

“Whatever. Shouldn’t you go eye-fuck your date?”

“Are you PMSing?”

“The picture of maturity,” Ruby snickered, and Dean found himself boxed in by her and her girlfriend. “Well? Aren’t you going to hang out with your boo?”

“You know what?” Dean shot glares at both of them. “I _am_! Have fun with princess Samantha, help him get that stick out of his ass!”

And, after receiving a well-aimed bitch face, Dean stalked off to do just that. The dance floor lit up, the music started and he had to circle around the outside edge to head where he’d saw Cas last. Thankfully, the man was still there - hanging out with Gabriel, Jessica (who had no qualms about last night, unlike his brother) and (gulp) Anna. Time to face the music, hopefully she was a little less _hostile_ around Castiel.

“Hey,” he greeted to Cas, just low enough for him to hear it, but not interrupt some ridiculously expressive story Gabe was telling (because Dean was awesome like that).

“Hello, Dean,” Cas immediately reached out and looped his fingers through Dean’s, tugging him closer.

Anna raised an eyebrow, but didn’t comment.

Dean barely made it to the punch line, which happened to be, ’ _But he said ’robot,’ not ’cum shot,’ so that was awkward_.’ Always keeping it classy, good old Gabriel.

Cas snorted while the other two women tittered at the last of his story, before Gabriel turned his attention to Dean. “I’ve been introducing Cassie around, but I can’t seem to get your brother hither. Still, Cas has made the rounds and is a hit, so you’re welcome, Deano.”

With a roll of his eyes, Dean pronounced out the obligatory, “Thank you, Gabriel,” while squeezing Cas’ hand. “Saw you weren’t even scared off by Ellen. Good work, babe.”

“She was supposed to be scary?” He frowned and looked confused, “She seemed like a wonderful woman. She appreciated my taking over your ‘bodyguard’ duty at the bachelorette party when you were too intoxicated to stand upright.”

“You little shit, I was _totally_ fine!”

“You couldn’t even _remember_ the name of the _hotel_ ,” Anna scoffed the reminder, “I don’t consider that ‘fine,’ by _any_ means.”

Dean had to bite his tongue, but before he could say anything, Cas did it _for_ him.

“I don’t blame him, he was thoroughly distracted. I _had_  made him the promise of fucking him through a mattress, after all.” Cas mentioned, like it was the most casual thing in the world, “I’m sure he remembered the name of _my_ hotel.”

“Cas,” Dean hissed at the same time Anna gasped, and both Jessica and Gabriel burst into a fit of laughter.

“Aww, Dean, you’re such a lovely blushing virgin right now,” Jess slugged him in the arm, while Cas changed his grip from Dean’s hand to his waist.

“Are you a born-again virgin, Dean?” A blinked with faux-shock, “I can change that whenever you want…”

“Castiel,” Anna warned in a low voice.

Thank god, Anna the prude was actually coming to his _rescue_ , this was the _first_ time he’d actually been grateful for her presence since she turned out to be such a crazy--

“My bet was after the garter belt. Wait until _then_ to seduce him,” Anna finished and tossed her red curls over her shoulder.

-crazy bitch he was _never_ grateful for because he was _stupid_ to think she was ever going to come to his rescue!

“Dean!”

He whipped around to see Lisa reaching out her hand and asking him with a bright smile, “Wanna dance?”

No, he _didn’t_ want to dance, he _hated_ dancing, but Anna was smirking at him, Gabriel was taunting him, Jess looked like she’d rather watch him suffer than help and _fuck_ Cas looked like he was about to shove him into a wall and devour him.

“Yep! Let’s dance, Lise.”

\----------

Of course, the next time Dean was looking for Cas, he saw the Meg had sidled up all nice and cozy to his side. For some reason, that really grinded Dean’s gears, and the multiple drinks in his stomach told him the way she was grinning devilishly his date was _not all right_. What the hell, why wasn’t she making goo-goo eyes at _Ruby_ , why was she with Cas? Just because he had been whisked away on the floor by Lisa, and then taken a couple shots didn’t mean--

So he quickly made his way over and plastered on a fake grin.

“See you two are having fun.”

Meg giggled and rested her elbow on Cas’ shoulder while she nodded her head, “Oh, I was just giving Cas advice, is all. Nothing for you to worry your pretty little head about.”

“Advice?” He echoed, because _that_ didn’t sound like anything good.

Cas nodded and took a sip of his mixed drink before casually stating, “Yes. I was just discussing with Meg how handsome you looked. And whether tonight, after I undress you, I should use your tie as a blindfold or a restraint to tie you to the headboard. What would you prefer, Dean?”

He promptly _choked_ on his drink, and Meg reached around to smack him on the back while cackling. “Sounds like he’d open to either, huh, Clarence?”

Dean _knew_ he was bright red, he _just fucking knew it._ And _goddamnit_ , his pants were _impossibly_ _tighter_ as he took in Cas’ innocent impression with wide-eyes.

“T-that’s not playing fair!” He hissed out.

“I’m not playing _fair_ , I’m playing to _win_ ,” and those long, confident fingers reached out to trail the entire length of said clothing article. “Which would you enjoy more? Being sightless, not knowing where I was going to touch you next... or being able to watch me, but unable to _do_ anything about it?”

Dean’s mouth was completely dry as Cas’ hand snaked around the tie and gave it a firm _tug_.

His voice dropped even lower, “Maybe we could do _both_ …”

Dean slapped his hand away, turned on his heels and charged off. Dean wouldn’t allow himself to be seen in the middle of the reception with a raging hard-on. He _knew_ if he was there for a second longer, there’d be a fucking _tent_ in the front of his dress pants. Could someone die of blue balls? Was that a thing? Because Dean was pretty sure that was a thing…

“You’re evil, Clarence, and I love it-” he heard Meg say to the man, before she finished with, “Let’s get another drink!”

\--------

So it had been Ash’s brilliant idea to grab an armful of beers and shotgun them outside, which the entire bridal party (all different levels of drunk) had totally gone along with. With exuberance and gusto, he may add.

And it was a _great_ photo op - the crew in their natural environment.

“Jo, you’re gonna get beer all over your dress!” Hannah gasped, scandalized at the thought, as she was handed a can (which she honestly had no idea what to do with).

“This ain’t my first rodeo, honey,” she winked and grabbed Benny’s pocket knife before looking around, “Everyone ready?”

“Hell yeah!” Garth cheered, and knocked into the glass door, dropping his beer that exploded all over.

Immediately ignoring him, Jo stabbed the aluminum, wrapped her mouth around it before handing the knife off and opening the can. It went around in a circle - the hiss of the beers being punctured, the curses and chokes of newbie’s and victorious roars of those who _didn’t_ make an _absolute mess_. Dean threw his empty into the trash and high-fived everyone who finished, and gave the finger to the losers. He was riding high on adrenaline and joking as people went for another round so he was distracted.

Which was _not_ the thing to be when there was a sexy dirty, dirty cheating motherfucker roaming the party.

And _that_ was how he found himself yanked around the corner of the building, shoved against the brick with a hot mouth covering his and hands grabbing urgently at him.

_Shit_ , he should have seen this coming!

But he _didn’t_ , which was why he fucking _melted_ against Cas’ assault and opened his mouth wide and kissed him just as ferociously in return. He was clawing at the other man desperately, rolling his hips and moaning into his mouth. And, hell, he must have been drunker than he thought, because off of a sudden, his leg was wrapped around Castiel’s waist, needy and wanting and Cas took that as a cue to _fucking lift him up._

He was pinned, stone wall unforgiving against his shoulder blades, but the grind of Cas’ hips between his legs was _well_ worth it. He knew Cas was strong, but the fact that he had hauled him up, and was _manhandling_ him like it was _nothing_ had Dean throbbing and straining against his pants until he realized what was happening.

“Fuckin a!” He grunted into the man’s mouth but _couldn’t stop kissing him_.

He whimpered.

Yeah, _whimpered_ , so sue him, he wanted Cas so bad it _hurt_ but it’s not like he could just bend over in the fucking lawn with a hundred people on the other side of that wall and-

The whimper turned into a much more unattractive sound as he struggled out of Cas’ grip and his legs struggled free. He was fighting to catch his breath, and as he finally caught sight of Cas - looking _thoroughly_ debauched, his cock twitched again to remind him that he could _have this attention_ , but was simply _choosing not to_.

“Fuck!!” He cursed, and pushed Cas away enough to finally breath his _own_ air. “I hate you. I hate you so much. I’m gonna fucking jizz in my pants, dude, and that’s not a good look.”

With a crooked smile, Cas stepped back into his space and dragged his palm along the front of Dean’s pants, “I don’t think there’s a way for you _not_ to look good.”

“Stop-”

“Do you _really_ want me to?”

And _that_ was the question. The _real_ question.

Of _course_ he didn’t _want_ him to. But his _pride_ … his… fuck. Fuck it. Fuck all this.

“Just… give me a second to calm down.”

Cas smiled victorious and raised his hands, taking a graceful step back, “Whatever you wish, Dean.”

But the fucker hadn’t won _quite_ yet.


	7. Chapter 7

Dean knew it was time to lay down the law, which was why he needed to pull Cas away from prying eyes. But this… was a really, really delicate matter. They needed to be alone enough to _talk,_ away from prying ears, but public enough to _not have sex_ with the threat of prying eyes. There was that fine line, because in the back of Dean’s brain there was a thrill that, _hell yeah, let’s just risk indecent exposure right the fuck now because I need it,_ but that would be rude to the bride and groom. Or so he told himself.

Normally, he wouldn’t give a shit, but today he did. Because it was Jo and Benny. Dammit.

Bathroom was a no go. Outside wasn’t either, because it had been so _easy_ to dry hump against that wall. Baby was even _more_ dangerous, because _god_ , did he want Cas spread out in front of him in the backseat while he rode his-

Motherfuckingfuck.

The music was too loud in the ballroom at this point, and there were too many _people_. Oh. Maybe the backstage area they had used to get ready for the wedding? That’s where everyone’s street clothes were… and people had been in and out grabbing drinks, and changing shoes and shit… They’d have enough time to stop what they were talking about, and _not enough time_ to get off or anything. Okay, yeah, _this could work_.

Dean grabbed Cas’ wrist and yanked him, none too gently, through the hall and back to the ceremony site. Then silently proceeded through the doors to the changing rooms. Castiel looked around casually as Dean took in a deep breath and started with:

“We can’t leave _yet_.”

“So you tricked me?” Cas frowned, but in amusement rather than resentment. “Did you bring us back here to pick up where we left off?”

“No. Stop that right now,” Dean collapsed down to one of the couches while Cas followed close behind on his feet. “So. There are money bets, right? Why not go in halfies with one of our faves _and_ make a profit?”

“Are you…” he raised an eyebrow, “ _Hustling_? Making bets? At a _wedding_?”

“Why the hell not! This was annoying to _begin with_ , and if we could rig the system, make some dough for a date night or some shit and get out of here early?” Dean wiggled his eyebrows. “Everyone wins! Well… that’s bullshit. Only a _couple_ of us win, but who cares about details.”

“Date night?” Castiel repeated, leaning down closer with a wide smirk on his face.

“Out of all my _genius_ planning, _that’s_ all you took in?” He huffed, but didn’t _really_ mind. “Yeah. So what. But we _gotta_ play it up, act like we’re gonna leave soon ’cause we can’t keep our paws off each other, so people start doubling up on their bets, and whoever we’re in cahoots with matches and gets the pot sweetened _just so_.”

“You act as though you’ve done this before,” he was more interested by the second. “Who do you think you’d want to be in cahoots _with_?”

“It’d have to be someone who betted in the middle… if it was too early, they’d _know_ we threw the game right away. And if it was too late, _I’d_ be pissed at _myself_ for staying the whole time when we didn’t _have_ to. But I think what we need is someone who can act and taunt people into betting _more_. Someone as sassy as us.”

“Did you just describe us as... sassy?”

“Better than horny. Because I could use _that_ word. Because I _am_.”

“I’m tremendously aroused,” Cas took another step to slot himself between Dean’s knees from where the man was still seated on the couch, “So I suggest we side with whoever you think can get away with it as soon as logically possible,” he leaned down close enough to feel the ghost of breath along his tingling lips, “Because I won’t be able to run on logic much long, I’m afraid.”

Dean shuttered as Cas gripped his forearm and slid down the length until he had control of Dean’s grasp. Which he languidly led to the front of his trousers and made Dean palm his half-hard erection. A deep rumbling moan escaped his throat as Dean’s hand acted _involuntarily_ and began stroking him. “Mmm,” he thrust into Dean's hand and grunted, “We need to plan, because I need to fuck that tight little ass of yours as soon as ‘logically possible.’”

There was only _one_ singular thing that kept Dean from unzipping Cas’ fly and taking him down his throat _right then and there._

“Dude. Did you just use air quotes while talking dirty?”

An abrupt belly-laugh broke from Castiel and he promptly stepped away from Dean’s (amazing) touch. “Let’s just get to work on this, Winchester.”

\---------

Castiel excused himself first to go to the restroom and ‘adjust _slash_ cool down’ while Dean took deep breaths in the room and dug out his phone. He tried to brainstorm, tried to remember _who_ bet on _what_ and who would have no qualms about _tricking_ the rest of their friends. While most of the bridesmaids and groomsmen were sneaky, he wanted someone who could stay mum about it _forever_.

He wouldn’t use this as a peace offering to Anna. He knew Ruby would _gloat_ about her victory as soon as it all was over. Gabriel would probably do that same thing, unless he was blackmailed, but the asshat had zero shame so that was out of the question. Jo would want to win - cut and dry - and would raise a fuckin’ _ruckus_ over the thought of cheating and tell everyone what they were planning and Dean would instantly lose. Because she was _just_ as prideful like that. He wasn’t partner-in-crime close enough with the majority of the groomsmen. The only three Dean felt comfortable with was Meg, Charlie and Jess…

But, at the same time, Meg had _Ruby_ as baggage. _And_ Charlie had _Dorothy_ as baggage.

And he had found out today that Jessica wasn’t _quite_ as innocent as she appeared… which made her the perfect little actress and her pretty little doe-eyes would make everyone fall for it when she raised the bet. Yep. He was into it. Now he just needed to talk with Jess and hopefully her ‘bet’ was an ideal _time_. He knew she thought he was going to make it past the toasts… and for some reason ‘before the dollar dance’ was sticking out in his mind, but he’d need to grab her to confirm before it got _too_ late. If he had a goal he didn’t _hate_ he could see it through. But Cas was really trying his _last nerve_ and Dean was pretty sure he was _two seconds_ away from jumping him on a fuckin’ _banquet table_.

“Hey there,” his brother’s voice snapped him out of his deep thoughts and he jerked up. “What are you doing back here?”

“Oh, uhh…” what was he supposed to say?

“Hiding from Cas and his aggressive woo-ing?” Sam suggested with a wink before sitting down on the couch next to him and pulling out his phone. “Maybe one of these days I’ll actually get to meet him without this whole clusterfuck.”

Dean mused over the idea of getting Sam as his partner in crime, but then realized, “You didn’t bet on us, did you?”

Sam looked up from where he was typing out a text and shrugged. “Nah, I thought about it. But then I thought it was kind of shitty everyone was putting stress on you when you’re actually _into_ this guy and you never get to see him, you know. Just thought it was a little disrespectful, especially because I know how glow-y and adorable you get when you talk about him,” he looked off blankly before finishing, “You don’t get a lot of time with him. It’s dumb there’s pressure.”

With an eyebrow raised high, Dean patted his brother on the back and honestly said, “Hey. Thanks, I really appreciate that.”

But the way Sam was zoning out told him that maybe, _just maybe_ , he wasn’t _only_ talking about Dean. Maybe he was talking about _himself_ too? Which, okay, was ridiculous as fuck, but there was _conviction_ when he spoke. And Sam had seemed _off_ all day. Even if he didn’t want to go into the mushy-nasty-land-of-girly-emotions, Dean felt like he had a big bro obligation, which prompted him to say:

“Hey, are you all right? Is there, uh, anything you want to talk about.”

Sam turned his focus and looked like he _wanted_ to say something but _couldn’t_. Which confused the hell out of Dean, because Sammy just loooved talking. Why wasn’t he doing that now? He was just _uneasy_ , and Dean’s protective instincts kicked in and he wanted to _help_.

“Yeah, I am. Just tired, I think.”

Nope. Not convinced at all.

“How late were you up last night?” Dean teased and elbowed Sam in the side a few times for good measure. “Musta been a rockin’ ménage if _you’re_ tired.”

With pursed lips, Sam scoffed.

Okay. So this _was_ what the _issue_ pertained to.

But he _still_ wasn’t talking about it.

Was this where Dean pushed, or just let it go? Dammit, he was _terrible_ at these things. But then, a flare of worry shot through Dean like a _bullet_ , and he quickly demanded, “You didn’t get hurt, Sammy?!”

“What?!” His eyes widened cartoonishly wide. “No! Oh, god, no, Dean, it’s not like that at all!”

“Well you’ve got me all worried now, because there’s _something_ you’re not telling me and the way you’re sulking and acting all skittish... it _looks_ bad, all right?” He turned his body on an angle to face his brother. “Give me _something_.”

“I-I’m fine, Dean. Really,” he stood up abruptly. “Just trying to work some things out in my head, is all. Let’s get back to the wedding?”

“Yeah-” his voice was clipped because now he was just _annoyed_.

Fine. If he didn’t want help or advice or anything, screw him. He could just keep sulking like a big baby.

\---------

The mutual understanding made it much easier to be around Cas. Now Dean didn’t have to _constantly_ be on guard and nervous hanging around the other man - which was cause to celebrate _all by itself_. But now… he could get Cas _back_. His date had been having all the fun, up until now, and it was obvious how badly he wanted Dean, so who was he to deny Cas what he wanted? Now that Dean had himself under control, that is.

Maybe, this shift in his mentality was all he needed...

As they sat together at the table, surrounded by Charlie, Dorothy, Hannah, and Gabriel they all slowly (Gabriel like he was in a starved third-world country) ate their dessert. Dean found Cas’ eyes on him the _entire time,_ so he put special care into audibly _moaning_ around delicious bites of the pie, and swiping his tongue to lick the fork clean. Cas’ gaze turned heated in no time at all.

In fact, the man had to clear his throat to inform Dean that, “You have some filling…”

“Where?” He blinked innocently, turning his body to block out the rest of the table, who were currently chatting about a new action movie that was coming to theaters. “Help a guy out?”

Castiel seemed shake himself off before reaching across and cupping the side of Dean’s face. His thumb rubbed over the sugary leftover and, before Cas could pull away, Dean reached up and stopped his hand. Instead of letting the man wipe it off (or, he wouldn’t put it passed _Cas_ to lick the filling off _himself_ ) he sucked the man’s entire thumb into his mouth. Cas’ eyes widened, as he swirled his tongue around the digit, and stared him, unabashedly, _directly_ in the eyes and hummed.

He nipped a little as he sucked, pulled away with a smile. “Thanks, Cas.”

With an intense glare, Cas yanked his hand back and shifted uncomfortably in his chair.

Yep, he was victorious. Mission: Give Cas Blue Balls, initiated.

Before he went back to eating, he unbuttoned the sleeves of his shirt and slowly rolled them towards his elbow. He could feel Cas’ eyes follow, hungrily taking in every _inch_ of exposed skin, which made him reach up to his collar. Instead of just loosing the tie, he completely undid the knot and unbuttoned the two highest buttons. He wrapped his hand around his tie and pulled it from his dress shirt with a ‘hissing’ sound.

He could feel Cas’ gaze just as heavy as ever, but didn’t acknowledge him _quite_ yet. Instead, he folded the silk fabric up, until it was a palm-sized square and presented it to Cas.

“Decided I want you to _tie_ me up tonight. No blindfolding. I wanna _watch_ you fuck me, want you to take me _anyway_ you want... while I can’t do a goddamn thing about it.” He pressed the cloth into Cas’ hand. “Do you want it too, Cas?”

There was only a _sliver_ of blue in Cas’ darkened eyes as he aggressively snatched the necktie from Dean and stuffed it in the pocket inside his suit. He looked as though he was now on the edge of breaking _himself_ , and Dean didn’t blame him. But Dean was _thriving_ in the feeling of _finally_ being in control around this sexy asshole. He even went as far as to set his hand dangerously high on Cas’ thigh before it was slapped away.

“I understand your need for revenge, Dean.” His words were clipped and deliberate. “But if this continues, I’ll have no choice but to make you pay when we’re alone tonight.”

“Punish me?” Dean whispered, leaning in close and flicking his tongue along the shell of Castiel’s ear. “That better be a _promise_ and not just an empty threat, babe.”

Cas’ eyes widened as he sharply jerked his head around and nearly head butted Dean. And fuck, as Cas bit his lip and slowly glanced down the length of Dean entire body, the man _knew_ he was in trouble. And as much as this had been about teasing _Cas_ he was beginning to get _himself_ all excited - and that just wouldn’t do.

So he leaned forward, gave him a single, lingering kiss then turned back to his pie.

Because, shit, how could he forget he had _pie_?!

While he started shoving it back into his mouth, he noticed a _knowing_ look on Charlie’s face, which he responded to with a wink. Cas was back to shifting in the seat next to him and deliberating crossing his legs while he downed the rest of his drink. Oh, revenge was a _beautiful_ thing.

\-------

Everyone was raising eyebrows at the fact that Cas and Dean _seemed_ to have a cease-fire. Which was making people _nervous_. After all, they had _money_ riding on this now, and Cas’ ‘ _help_ ’ with their little bet seemed to... cool down? And that would _not do._ But what were they really _supposed_ to do? Tell Dean how fucking hot Cas looked? How he had one hell of a catch? How much of a god he was in bed?

Fuckin’ _duh_.

Dean _already_ knew all these things, and it _was_ tough shit he couldn’t take Cas home right then and there. But… they’d already decided things. And luckily, some of the landmarks and people losing their wages were about to go down. Starting with Anna’s. Because, _yep_. They were coming up on the _tradition shit._

Except… Jo _wasn’t_ traditional.

Or, she _was -_  but was currently a little _too_ intoxicated to realize that the bouquet toss was supposed to go _before_ the garter belt, since she was _currently_ ordering all unwed men out onto he dance floor...? No one was dumb enough to correct her. There would be hell to pay.

“Come on, bitches!” Jo called out, and the women were quick to leave, looking a little confused but stepping aside anyway.

They hadn’t made much of a big deal about the _removal_ of the garter belt, because everyone _knew_ those two were much too obsessed with each other, and if they _allowed_ themselves to get into it, the event would quickly turn into a porno. So, now they were poised to toss it back, and Dean found himself grudgingly pulled onto the dance floor with Cas. But why was his date wearing a smart-ass grin?

“Don’t tell me you’re trying to catch it?” Dean raised an eyebrow, “Because I’ll _seriously_ be judging you.”

“No.” Cas paused for a moment while others trickled onto the dance floor. “I just know something that you don’t.”

“I kind of hate the sound of that.”

Castiel wrapped an arm around Dean’s back and chuckled warmly, “Don’t worry. You’ll approve, I promise.”

“Ready?!” Jo shouted over the noise of the crowd.

Cas and Dean stayed towards the back corner when Jo wound up and chucked the garter belt over her head. They watched it sail, _dangerously close to them_ and then land.

_Right_ on top of an unsuspecting younger Winchester’s _head_ , who was in the middle of a conversation with Bobby.

He jerked in alarm and reached up in confusion - having not even been standing _on_ the dance floor - before shooting an incredulous look at Jo. “What the hell?!”

“Nice catch, Sammy!” She cheered and gave him a thumbs up.

Sam looked around at those surrounding him with bafflement, and concern to the frilly lace garter down in his hand.

“And nice aim, Joanna,” Cas whispered in Dean’s ear.

“Oh, God.”

\--------

Dean excused himself from his reign of terror upon Cas’ dick (for a hot sec, anyway) to find Jessica before the bouquet toss. They had things to work out, after all. When he whispered his idea in selecting Jess as their candidate, Cas confirmed that was the right track, and if she had indeed bet before the dollar dance they’d be leaving within the hour. Which was something they could work with. Or, they’d _force_ themselves to work with. So Dean walked along the floor until he found the chipper blonde and asked, “Shot and a dance?”

“Why, Dean,” she grinned, and poked him once in the shoulder before taking the small disposable cup he was holding out to her. “You know how to romance a lady. Too bad you’re taken.”

“While I’d love to invite you home with us,” he teased, “I’m kinda bad at sharing.”

“Hah,” she laughed, raising her cup in a toast, “You’re not the only one.”

They both threw back the shot of whiskey, but then what she’d said sunk in. “ _Wait_ , not the _only one_?”

She easily tossed the cup in a garbage can five feet away and shrugged, “How about that dance?” Jessica led him out to the dance floor and they easily fell into step with each other before she giggled out, “Yeah, Sam’s been giving me the evil eye today without meaning to, I think,” she thought aloud. “I think he’s actually really into Gabriel.”

“Huh,” Dean was straight up _confused_. “I thought that… uhh… when I think wild threesome I think…”

“Girl’s holes get stuffed? We ran a train? Something like that?”

“Ahh! Jess, I never thought someone could make _me_ blush, but _you_ just did, you little vixen!” Dean stammered out, shocked by the brazen comment. “But, uh, yeah more or less?”

“Nah, nothing like that. I got in some hot, threeway making out time, but - not gonna lie - I got off watching _them_ , that's kinda a kink of mine,” she smirked, and even though Dean felt like he puked in his mouth a little, he was… _intrigued_? “I guess after I passed out, they went for round two. So, I think I’m more or less a first-hand witness to Sam’s big gay freak out and I don’t know _how_ to snap your brother out of it. It’s _obvious_ he really likes Gabe. I mean, I may have been three sheets to the wind, but _he_ was _sober_. So I don’t know if his issue is that he can’t blame it on booze, or he’s thinking Gabe’s a whore but I happen to know from talking to Gabe that yeah, sure he’s a man-slut but he also really likes Sam. And Sam won’t really talk to him.” She rolled her eyes while Dean spun her around. “So, there’s _that_ little bit of drama happening.”

“Wow-” was the only coherent thought Dean could form in his brain. “That’s… tough. No wonder why Sam’s acting all fuckin’ weird.”

Dean remembered the words Sam had spoken - ‘ _You don’t get a lot of time with him. It’s dumb there’s pressure_ -’ and now he realized … maybe Sam _had_ been speaking in regards to himself as well? Was _that_ how he felt about _Gabe_?

It made sense. The two didn’t really have time to talk, no privacy, no immunity from others coming and interrupting and Gabe would be headed back to Chicago in no time flat…

“Yeah. That’s _definitely_ why he’s been acting weird. Shit.”

“Mmhmm,” Jessica confirmed, “So I thought I should fill you in, because if anything could get through your bro’s thick skull it would either be you… or Cas talking to Gabe? It‘d be sad to ruin a good thing. They‘ve got this freakin‘ _electric_ chemistry, just like you and Cas. Kinda a shame there's all this pouting and unrequited longing happening. Gabe‘s been trying but… yeah.”

“Yeah,” he nodded. “We’ll do something about this… now that everything makes sense, we’ve _gotta_. Hopefully I stick around long enough,“ Dean thought out loud, an then realized there was a _reason_ he had sought Jessica out to begin with!

“Oh, speaking of filling in, how would _you_ like to win a bet?”

Her eyes nearly _glittered_ in mischief, “Oh yeah? I‘m listening!”

\---------

Jessica was a goddamn _genius_. While everyone else had been noticing Cas and Dean’s _lack of_ PDA, and thought it was them ‘getting in control’ of themselves to reach the end of the night as a pair with a common goal, Jess spoke her ‘internal monologue’ aloud. She was chatting with Meg, saying she still had a _gut feeling_ something would happen and they’d run off into the sunset before the dollar dance. Or ‘ _at least she really hoped, because here she was, so sure of it, she was_ about _to raise the bet_.’ Meg was _stubborn_ , and she knew _Dean_ was _stubborn_.

So Meg was one of the only people who thought Dean was going to last right up until last call, but then bolt before clean up. So Meg confidently stated, “They’re obviously behaving, Jess. Deano fluttered his pretty little eyelashes and convinced Clarence to hang tight with him until the end. Obviously they’ll be able to hold out until _after_ the dollar dance.”

Jessica ‘frowned in thought,’ “I don’t know, I just really _really_ think after the bouquet toss and the dances start they’re gonna hightail it, Dean‘s been so _romantic_ about tonight, maybe he‘s falling in love?,” she ‘psyched herself up’ and nodded resolutely.

“Hah! Dean isn’t gonna turn into a wimpy princess over a fuckin’ _bouquet toss,_ Jess.”

“He’s _sensitive_ deep down! I _know_ it! This is the thing that‘s gonna make them snap-”

“Whatever, I’m doubling my bet! He’s _not_ gonna get all melty over this _bullshit_.”

“No way,” Lisa joined into the conversation, “I bet before last call. I want in on the doubling, Meg is _right_. They’re not gonna cave over something _sappy_. And you _know_ they’ll stay through the dollar dance just to embarrass Jo and Benny.”

Jessica’s ‘jaw dropped in horror.’ “Guys! Well, shit. I’ll double mine too, then!”

All of a sudden, a few more people overheard the latest news with Jess waxing poetry about their whirlwind romance, destined to be set in stone by the old wives tales, and jumped in - balls to the wall. Yep. Jessica was a goddamn _genius_.

And, okay, maybe she knew him a _little better_ than anyone else, because these days… he _was_ getting to be that sappy. But no one had to know that…

\---------

Apparently, catching the bride’s bouquet was a blood sport.

Dean never knew quite how serious it was taken until _now_ , but he’d never been close enough to crazy single women until now, either. And apparently, this old tradition was mixed with modern magic and was a sure-fire hoodoo way to ensure happiness, which he’d been oblivious to his entire life, FYI. It was actually really terrifying, if he was being honest.

Hell, some women were mumbling about _strategies_ , as one would a football play - except... there was no referee to throw down a penalty flag, and these women were _not_ playing fair. And there were _multiple_ reasons they were gunning for this flowery-magic. Some of the women wanted the bouquet because they wanted a happy relationship, as it was supposed to be in the weirdo myth.

But since Jo had fucked up the _order_ and tossed the garter belt _first_ , which his brother caught…

… most of these thirsty bitches wanted _Sam_.

Who was looking uncomfortable as hell along the edges of the dance floor, as the women huffed and puffed and prepared to blow each other’s house’s fuckin’ _down_. Some had opted to leave their shoes on the side - a couple had even _ripped holes_ at the bottom of their _panty-hos_ so their bare feet had traction on the fuckin' _ground_.

There was a terrifying fire in Becky’s eyes, a hunger in Bela’s, a teasing quality in Jess’s (while she deliberately sent a wink over to Sam) and then not to mention the _herd_ of  _widows_ and _divorcees_ on the floor, too.

Sam always had a way with the _cougars_ , and those women had _sharp claws_. It was like the white-caps of waves in the ocean - only it was the freakin’ permed and poofy hair of the old women. About to come in like a Miley-sized wrecking ball.

Ruby and Meg were a tag team, just like Dorothy and Charlie, each setting up on opposite ends of the ball room to double their chances and cover more field.

Dean was on the edge of his seat with Cas’ hand in his as he leaned forward and waited for Jo to wind up.

The massive grin on her face told them as well this was gonna be _chaos_ and she was _more than a little_ excited for it. None of the men could have given two shits about the garter, but the women were going to make up for it in _this_ performance. With bells and whistles roarin'.

“ _Breathe_ , Dean,” Cas teased, as he ran a thumb along the outside of the man’s hand. “This happens at all weddings.”

“Do you _know_ these women?!” Dean hissed, “They’re _animals_! We need to make sure a fuckin’ EMT is on stand by or something.”

Cas paused thoughtfully, and then agree, “You’re correct. Just look on the bright side - at least Jo is throwing the bouquet and not _in the crowd_ to _catch_ it. Or someone would end up with a broken bone.”

“Aw, Cas, you’re such a smartie,” Dean leaned in and kissed him once on the cheek. “That’s true, though. No one gets in the way of her on a mission,” he shivered at the thought. “Oh, shit. Here it comes.”

Then everything in the room _froze_.

The spectators stared - as the bride turned her back - the bridesmaids, grandmas and housewives on the floor alike - _eyes on the prize._ She rocked her arm, once… _twice_ …

And then let it _fly_.

The clicking of heels, some screeching battle cries and flailing limbs _crashed down after the bouquet_  like zombies to a runaway human, hungry for flesh. It was a _pile up_ \- similar to a gory accident on the side of the express way, and of course, no one could look away. There was screaming, cursing, kicking within the giant accumulation of love-sick women and no one was coming out victorious.

Should someone break it up?

What if someone really _was_ seriously injured?

Dean had _cringed_ at the amount of acrylic ’stiletto’ nails making a debut at the wedding and _knew_ they could be a tool of homicide.

Suddenly, like someone setting a volleyball up against the net to be spike, the bouquet _popped up_ from the crowd and _everyone reached up_ to grab it.

Except… everyone was struggling in the riot. And they'd become _too_ tangled up to grasp how _high_ a distance it flew.  It was a battlefield, constricted in nylon, tulle and soon-to-be broken dreams

Which allowed _someone_ to casually walk by, completely avoiding the battle royal, and _pluck_ it from the air.

And it was _fucking Gabriel._

He whistled with a skip in his step as he continued to walk along the length of the ballroom and away from when the women were grunting, moaning and screeching obscenities and made a B-line for Sam. Dean squeezed Cas’ hand a _little_ _tighter_ as he watched Jo cackle, Benny smirk, and Gabriel look like the cat who caught the fuckin' canary.

His brother’s facial expression morphed from shell-shocked, to nervous, and then to embarrassed when Gabriel reached out his hand.

“So, once these savages clear off the dance floor, it’s our turn, yeah?”

“This isn’t fair!” Becky shrieked from where she's finally pried (torn, _whatever,_ she was livid) Lisa's bracelet off her sash and stalked over to Jo. “This is a girl’s only tradition! He’s not allowed to catch the bouquet! He didn’t even _try_!”

Benny and Jo exchanged looks.

“We’re equal opportunity here, Becks,” Jo winked. “And besides, that’s what I call a badass interception.”

“Hell yeah,” Benny raised his glass. “I’ll cheers to that!”


	8. Chapter 8

The best part of Gabriel pulling Sam to the dance floor was no one (outside the small group of Cas and Jess) knew _what the fuck_ was going on. So Dean’s obnoxious snickering was raising a few eyebrows. But… come to think of it... this seemed to be _deliberate_. When Cas had mentioned Jo had ‘nice aim,’ the wheels began turning in Dean’s mind. He wouldn’t put it passed Cas or Jess to talk to the bride, and by the way she was grinning like a Cheshire cat _someone_ had filled her in.

And, kudos to Jo, the devious little minx.

She’d reached a new level of matchmaking. Because, after all, no one was going to refuse a bridal tradition on fucking _Joanna’s_ wedding day.

The music changed to a slow song, and Dean was suddenly reminded that they had a plan to follow. So he whipped his attention back to Cas and tugged on the man’s hand, “So that bouquet toss was romantic, huh,” he remembered Jessica’s spiel. “Dance with me?”

He raised an eyebrow and stated blandly, “You hate dancing.”

Dean leaned in and hissed in his ear, “But I love money. Get with the program!”

“Oh!” His eyes lit up in understanding and approached the floor. “My apologizes. Yes, I’d love to dance.”

\------------

Sam’s heart was doing fuckin’ Zumba in his chest when Gabriel strolled up to him, with all the confidence in the world, and told him they were dancing.

There was nothing _questioning_ in his tone, it was a statement and Sam hated that he had no where to hide this time. If he refused... people would start talking. And in his paranoid brain, if he declined, everyone would _instantly_ be filled with the divine knowledge he’d slept with Gabe the night before.

Twice.

Goddammit!

So he tried to plaster on an amused smile, as his clammy hand was gripped by Gabriel’s, and headed out on the dance floor. Thankfully, other couples were filtering on at the same time (surprisingly Dean and Cas were, too?) so there wouldn’t be attention on them. Or so he _hoped_.

Of course, Gabriel pulled them front and center because he was a cocky asshole and wrapped his arm around Sam’s waist.

“So,” he began casually, “You’ve been avoiding me, huh, Sasquatch? What’s that all about?”

“I haven’t been avoiding you,” Sam tried to hold his gaze, but Gabriel’s eyes were alight with mischievous and he knew this wasn’t going to end well.

“I’m not an idiot. So, was it the awkward morning-after that gotcha down, or the fact that you maaay not be able to keep your hands to yourself, now that you know how glorious I am in the sack?”

Sam’s head whipped from side to side looking for eavesdroppers (while he blushed a neon pink) and exhaled a sigh of relief when he realized no one was close enough to hear the brazen comments. “You can’t just _say_ _that shit_.”

“Why not?” He pouted and didn’t stop his hand from wandering a little _lower_ on Sam’s waist. “You’re not answering me. Really, this is no fun when it’s all one sided. What’s going on in your head?”

“I-I, uh. I’m awkward, I guess, but not ashamed or anything like that,” he finally admitted aloud.

“So you wanna go for round three?” The mischief was back, 100%, but beneath the bravado there was an open… longing?

Sam rolled his eyes. He honestly had no idea _how_ to handle this man, and maybe that’s why he found him so… interesting? Alluring? There were a lot of things he found Gabriel, but he couldn’t put together the pieces that answered _why_ he felt all these things. And he hated that. _Obviously_ , he’d be into round three. If he agreed to a fucking round two, that was a bit more than breaking the seal, right? Was Gabriel just trying to get under his skin, or did he actually want to see him tonight?

“It’s a simple question.” Gabriel interrupted his thoughts again.

“Yeah. But it’s not a simple answer.”

That had the other man confused. “Well, you’re mine for this entire song. So I’m gonna get it out of you. Wanna do this the easy way or the hard way? Both can be different kinds of sexy.”

With a dramatic exhale, Sam narrowed his eyes and just decided ‘fuck it.’ He blamed the open bar for his actions - this time. Last night… he didn’t have that excuse. So why did he even _think_ he had to hold back now? It’s not like - as much as it hurt - he probably would see him ever again.

“Of course I’d go back with you, but I don’t know what I’m doing because I actually friggen _like_ you, all right? And it sucks you’re leaving and headed back to Chicago tomorrow. You came out of nowhere, basically knocked me on my ass and now I don’t know if I should just ignore you, because you’re gonna leave anyway, or spend time with you while I can and cross my fingers I don’t like you even more than I already do!”

Gabriel blinked. “That’s it?”

“Is what it?!” He was getting snappy now.

“It _is_ a simple answer, moose. You like me. I like you. Wish you would have told me _that_ was the problem sooner, because then I could have been groping your fine ass all wedding!” He emphasized his point with a firm ‘twack’ on Sam’s butt, that made him turn scarlet. “I’d be _more_ than into seeing where this leads. I’ve got frequent flyer miles, a fuckin’ phone and a computer with a webcam,” he wiggled his eyebrows. “Unless you’re allergic to the words ‘long-distance’ I say we go for it.”

“What?” Sam’s feet stopped moving until Gabriel kicked him, and began dancing again. “You’re… serious? I don’t believe you. You’re drunk and saying things that you don’t mean and-”

Gabriel quickly grabbed the back of Sam’s neck and hauled him down for a kiss. He was too caught off guard, too surprised to know what was happening _until it_ _happened_ and then he couldn’t focus on anything but the feel of Gabriel’s soft lips against his. So he gave in. He opened his mouth, ever so slightly, to tell the other man that _yeah_ this was all right. The rest of the world faded away and he clung onto Gabe for dear life. Shit, it was kind of a fireworks, heart-skips a beat moment, until he was snapped back to reality by cat-calls and whistles.

“Fuck,” he pulled away abruptly, and focused on Gabe’s victorious face, rather than the people who were staring.

Because he knew a cubic shit-ton of people were staring.

But Gabriel didn’t seem to mind, and that… in some strange way… made _Sam_ not mind. And soon, as he'd hoped, people calmed down. Thank god. He didn’t want to head for the hills, and the way Gabe was holding him in place made it physically impossible, anyway. That didn’t mean that he wasn’t a whole new obnoxious shade of scarlet. Still, the comforting hand Gabe still held around the nape of his neck soothed him.

“See. I’m serious,” he clucked his tongue, “And I take it you are, too? At least a _little_ bit.”

“We’ll talk about this more,” Sam’s voice was final, and he adjusted his grip, “Let’s just finish this damn dance.”

\-----------

“Uhh…”

“Interesting.”

“Yeah, that’s one word for it,” Dean cleared his throat, as he shifted his hold on Cas ever-so-slightly and scooted around so he _wasn’t_ gawking at Sam and Gabriel. He needed to feel like he could give the two a little more privacy.

Not like they had privacy, by _any_ stretch of the word.

They were on the damn dance floor, at a goddamn wedding, and they were the focused-on dance _couple_ at the minute. And yet, Gabriel had decided it was the peeeerfect time to have his tongue down Dean’s brothers throat. Because that was just so _logical_. Still, Gabe was never one to operate on logic, so there was _that_.

Castiel leaned forward and his breath tickled Dean’s ear, “We can get out of here soon, Dean" he nipped his lobe lightly. “After all, we were supposed to be moved by the romance of the bouquet and garter toss bringing lovers together. Shall we make a scene, as well?”

“Mm,” Dean butted his head along Cas’ jaw, to get better access to his neck and kissed his throat, “I could be into that…”

Then the music changed.

The dance was over, and it was time for them to vamoose and for Jessica to collect her reward.

Well. At least, it _should have been._

Except for the fact, that Dean’s fucking _moose of a brother_ decided _this_  was the perfect time to grab his arm, tell him, “We need to talk,” and _yank him away._

Oh, fuck, no!  No, no, no, no.

Dean’s eyes were wide as he was dragged away from Cas, who was looking equally flabbergasted, being left in the center of the dance floor by himself.

The last thing Dean saw, before being jerked around the corner to have a goddamned ‘heart-to-heart’ was Jessica giving him a _‘what-the-fuck_ ’ face and charging to take his place with Castiel on the dance floor. Oh, shit. This was _not_ going according to plan.

\----------

Shit. Shit. Shit.

Dean was in fight-of-flight mode when he found himself in the backroom with his brother, who had taken to pacing back and forth and taking deep breaths. He was trying to steel his nerves to speak to Dean, and Dean wanted to yell at him to just _get on with it_. He needed to jet. Right. Now. But he couldn’t leave Sam.

But… could he kick him? Smack him a little?

Tell him to _spit it out_ already?!

“Dean… I, uh,” he finally stopped his pacing and ran a hand through his hair. “I think I _really_ like Gabe.”

“Yeah, I noticed that,” Dean’s words were rushed.

He needed to get back out there, back to Cas, back to-

“What do I do? Do you think we can do long distance? Should I even _try_? It’s been a while since I’ve even _thought_ about a relationship, but with him I feel like it… may be _possible_?” He looked so nervous, with those big puppy eyes and deflated posture. “What would you do?”

“Go for it.”

“Really?” His eyes brightened, at the sound of those words.

“Yeah, totally go for it, dude.” Dean made a hasty move to leave, but Sam reached out and grabbed him.

“Hey. What’s up with _you_?” And in a flash, his puppy eyes instantly transformed into a bitch-face. “I thought you were worried about me. And now it looks like you’re just trying to get away from me. You say ‘go for it,’ but you’re acting like you hate Gabe. You acted like that before when you introduced us, and part of my problem is I want _you_ to be all right with him. I don’t know, you know him better than me… do you think it’s a good idea?”

It was then, that Dean knew he couldn’t just shuffle out of here like he wanted to. He _owed_ this to his brother - because Sam was seriously invested. God knows _why_ , but he was. So Dean took in a deep breath, pulled out of Sam’s grasp, and dug his hands in his pockets.

“Well. Gabe’s an ass.” Dean watched Sam shrink in place a little, “ _But_ not in a bad way. He wasn’t a sleaze in Chicago, didn’t take advantage of any of the girl’s at the bachelorette even though they were three-sheets, hell, did a better job than _me_ watching over everyone and making sure they were safe. He’s responsible, even though he’ll fight tooth and nail to pretend he’s not. He’s the one who made it all right between me and Cas, he’s the one who defended me in front of Anna. Hell, he’s been annoyingly asking about you and worried all damn night while you’ve been hiding from him. So, Gabe’s an ass. But he’s the good kind.”

And, shit, if that fucking _glowing_ smile on Sam’s face didn’t make Dean feel damn good about himself, he didn’t know what would.

“You don’t think I messed things up by sleeping with him last night?” Sam fiddled with the sleeve of his button-up.

“Uhh, hellooooo,” Dean reached out and smacked his brother in the arm. “Who the hell do you think you’re talking to? I did the same thing. At least you did a solemn, graceful walk of shame, rather than make a scene, rack up a bill of over a hundred bucks and give the guy a fuckin’ heart attack. If _I_ got myself out of my mess with Cas, your little vanilla threesome is just that. Easy-peasy.”

“'Vanilla threesome,'” Sam echoed with a snort. “Our lives are fucked up, you know that.”

“Hey, as long as we come out on top,” Dean clapped Sam on the shoulder and genuinely smiled.

“What’s this about topping?” A new voice asked, walking into the room. “Because I know, from a _very_ reliable source that _you_ are a bottom, Deano.”

“What do you want, Gabe,” he spun around and glared.

“Wanted to talk to the Moose. Oh, and let you know Cassie looks pissed,” he walked across the room, winking at Sam before turning his attention back to Dean. “The dollar dance has started.”

“Fucking hell!”

\---------

Dean sulked back out to the room. If there was time, any chance in hell that he could have made it, he would have sprinted like an Olympic fucking athlete, but knew he was fucked. Gabriel’s words were final. They cemented his doom, and now he felt as though he was walking through the twine decorated halls, to a very rustic-chic guillotine. Especially when he caught sight of the icy glares both Cas _and_ Jessica were shooting him. They were both gonna cut the cord and run off into the sunset together.

But what the hell was he supposed to do?!

It was his fucking _brother_ , for crying out loud!

Sam got emotional. He needed a shoulder to cry on, or else he would have drowned his fucking sorrows in the punch Meg had spiked at the beginning of the night. That shit was near-lethal by now.  He wanted his brother alive, thank you very much.

So he shook himself off and walked towards them.

Neither of them offered him a greeting.

Just kept staring.

And, okaaaay, this was awkward.

“Silent treatment?” He grumbled. “Really, guys? I had a sister-crisis, and Jess, _you’re welcome,_ their big gay love fest is official, all right?!”

She leaned in towards him and growled, “Their 'big gay love fest’ isn’t worth my two hundred bucks, Winchester!”

“T-Two hundred?” He echoed. “It, uh, got up that high?”

“Because you fucking _promised_ me, and I did my job. Fantastically, I might add! You owe me that money,” she stabbed him in the ribs, her shellac'ed nails doing worlds of french-tipped-pain. “So you either pay upfront, or you figure some other plan out, and _soon_.”

“Yeah,“ he yelped and quickly ran away from her, because Jess was pee-your-pants terrifying right now.

Castiel wasn’t looking any more welcoming. But... at least he wasn't armed with heels or a clutch with an angry-looking silver buckle that'd slice his forehead clean open...

However... Cas _did_ go as far to cross his arms and narrow his eyes something _fierce_. “So. How far does this push back our departure?”

“Fuck if I know! Gimmie a second to think, Jesus Christ!” He glared right back, and sighed all the heavy breath from his lungs. “Sam fucked us over… even if he didn’t _know it_. And Sam hasn’t made a bet and entered the pot yet. Maybe we could use him?”

Cas huffed and rolled his eyes. “Wishful thinking.”

“Excuse me?” He raised an eyebrow, “I think that’s a _great_ plan! Quit being fussy, babe, we gotta think positive! What’s your problem!?”

“Besides the fact Gabriel announced to me he was going to _‘find the giant, shove him in a closet, and fuck his brains out,_ ’” Cas quoted, his voice completely deadpanned. “Nothing.”

Dean pivoted on his heels, took two steps towards the wall, and banged his head against the wood. All right. Maybe they were fucked. Unless there was another giant frolicking about the reception he hadn't noticed before? A guy could dream.

\------------

He didn’t care who noticed. Nope. Didn’t care one bit. Dean had raised his sulking to a new extreme. He'd be surprised if there _wasn't_ a dark storm cloud literally hovering over his head. Hopefully it'd start raining and it could drown him. That sounded like a flawless idea... He had parked his ass right up in a cheap, plastic chair on the edge of the dance floor - beer in hand - and stared out into space. He couldn’t think of a plan. Couldn’t think of a way out of this. Maybe it was because his brain was too whiskey-soaked. Maybe it was because their initial plan was so _brilliant_ , he had used all his smarts on that one alone. But… he _did_ know that Cas was getting _antsy_. He was fidgeting next to him, and he didn’t blame his date one bit.

They _both_ wanted to leave.

But, for now, they watched as Benny and Jo danced with the long lines of people, offering up Washingtons one by one. Dean thought it was _stupid_ \- the only place where ones should be flung around like this was a goddamn strip club.  Mm, Cas would make the sexiest stripper...  What he wouldn't give for a lap dance, all swiveling hips and - shit!  He needed to stop this right now... Focus, on the wedding... on the plan on the... God. This was torture. It seemed to go _on_ and _on_. At minimum, three songs had passed. And Dean was no closer to a stroke of genius than he had been at the beginning of his pouting session.

All he’d managed to accomplish, was draining two more beers.

And ignore his date.

Everything had gone to hell.

He felt a warm hand on his shoulder, the first thing in a long time that soothed him, because he’d recognize Cas’ touch anywhere. He leaned into it and sighed. All right, so maybe his date was getting over it? He dared to glance at the man, and when he did, saw that Cas' focus was still on the dance floor. But his grip was firm, and worked at massaging the knots out of Dean’s shoulder. And, damn, that was nice. He only wished they were _alone_ , and that hand was massaging something a little _lower_ …

“So…” he began to say, letting his chin brush against Castiel’s wrist. “You come up with any new direction to take this? Because I believe I’m fresh out.”

“Pay off Jessica. And get out?” He suggested, eyes never leaving the dance floor.

“Sorry about all this,” he grumbled, “It’s Gabe’s fault.”

“It’s Sam’s fault.”

“It’s _both_ their faults. Whatever. I’m gonna go dance with Jo. What’s another dollar when you owe another blonde two hundred?” He grumbled and shrugged off Cas’ hand before he stood up.

Maybe he was being childish, but he was in a bad mood all of a sudden. The line to the bride was significantly shorter than it had been so far tonight, so he dug through his wallet in his suit coat before producing a single. He kept it in his palm while he strolled up and joined the line. And, fuck, he was _right behind_ Anna, and didn’t notice until the flash of red hair caught his attention along with the inquisitive face.

Her arms were folded in front of her when she commented, “Cas doesn’t look happy.”

“Yeah, yeah.” His answers were clipped. He didn’t owe her an explanation.

“How did you piss him off?”

Great. Sister-zilla was coming out, loud and proud, and attacking Dean. Just what he needed.

“Don’t look at me. It’s all you guys' bullshit betting that’s got us all tense. Not my fault.”

She didn’t seem convinced in the least. “He hasn’t been upset until now.”

He didn’t even give her a response, because she was up next, and Charlie (who was collecting the money right before they were lead to the bride) reached out to take her dollar. Anna’s eyes never stopped glaring, right up until Jo smacked her on the arm and dragged her out. At least, now, Dean had Charlie to chat with for a hot sec.

“So, Sam and Gabe?!” She rushed to get out, voice giddy and devilish at the same time, “I didn’t see that one coming! Where are they now?”

“Where do you _think_ ,” Dean winked, because Charlie put him at ease. He could let go of at least a little bit of the tension when he was around her. “Turns out, Gabe’s the vacuum.”

“Friggen Dirt Devil.” She cackled, “Now, what’s _your_ trouble in paradise?”

“Just wanna leave.” He sighed and cracked his neck, feeling the tension of the entire day soak in, and leave him heavy. “I’m gonna be beat by the end of the night if I stick around, I’ll probably drink my feelings, get whiskey-dick and be all sorts of a failure with Cas in bed. Then, I'll be so embarrassed, I'll never have sex again, have to be a monk somewhere and they'll make me try and find God.  I don't wanna find God.”

“Wowie.” She blinked a few times, eyes wide. “That escalated quickly.”

“My friggen _life_ escalates quickly!” He was being dramatic, but he didn’t care, “Charlie, save me, I can’t even think anymore!”

She looked thoughtful for a second. “Meet me at the bar, after these shenanigans are over and I’ll try to think of something, all right?” She reached out her hand. “Now, pay up, Winchester!”

Dean slapped the single down in her hand, right as Jo was waving Anna off, and coming over to him with a shimmy of her shoulders. As she reached out and snagged him, Dean was almost _positive_ he saw Cas, on the other side of the room, reach into his own wallet to hand Jess off some money. Well, maybe things _were_ looking up. If that debt was settled, they could get out of here whenever?

Unless, he was just paying _his_ half… then Dean would most _definitely_ still need Charlie to help him with some kind of plan. He didn’t just have a spare hundred laying around…

\---------

“You better be decent!” Snapped a very feminine voice through the back halls of the banquet hall. “Because, ready or not, here I come.”

Just as soon as her voice started to echo, two very debauched (yet fully clothed) men tumbled out from a back room, flushed but welcoming.

“Hellooo, darling Jessica!” Gabe greeted. “What can I do for you this lovely evening?”

Jess raised an eyebrow as Sam hastily buttoned his trousers and explained, “As much as I’m happy you two _finally_ got passed the awkward and dove right into the honeymoon stage, this bullshit cost me some serious cash, and I’m here to collect.”

“Say whaa?”

“Very eloquent, Sam. I see Gabe did a very good job of fucking you stupid.”

“Woah, woah, don’t get all hostile,” Gabriel cut her off and reached into his pants, “Now, what’s going on and how much do I have to pay you to cease and desist killin’ my afterglow?”

“Two hundred,” she reached out her hand, expectedly.

“Uhh, can you explain this?” Sam balked, as Gabriel started counting out twenties without hesitation.

“I’d be happy to-” she eyed the cash and dove in, head-first, with the story.

\----------

Charlie, little saint that she was, waited patiently at the bar with a pair of shots and a pair of drinks. Dean joined her and immediately asked, “So, come up with anything good in that genius little brain of your, my Queen?”

They took the shots while she made a tilting ‘so-so’ motion with her hand. After the burn faded from their throats and she exclaimed a “wheeew!” she stated, “Well, it’s kind of a situation about pride vs. whiskey dick, am I right?”

“Yeah,” he leaned against the bar. “So… I know this is an asshole move, but I can tell you now - since it crashed and burned. Moral of the story, Cas and I went in with Jess and were gonna throw the game, so she won the money, and split it with her. But then, Sam had to pull me aside when we were leaving and we missed our chance and now we owe Jessica money because we promised she’d win.”

“Hah!” Charlie threw her head back and laughed. “I’m kind of impressed with that, actually. And it’s _total_ karma that you got screwed over. So, let me guess, you’re wanting to figure out a way to get the money back and pay her off?”

“Yeah, I mean-”

“I already did,” Cas’ voice interrupted him as he walked up and stood next to them at the bar. “So, in reality, we can leave whenever. Unless you’re still going to be prideful, which I hope you’re not.  Or else I'll be extremely disgruntled and shall have to start my seduction all over again.”

“Awww,” Charlie rested her chin on her palms, “You’ve got the cutest boy ever. Taking care of you like that. You guys should skedaddle, 'cause then I’ll be the next one to win the bet. So vamoose! Pronto!”

“Always so selfless, Char.” Dean snorted, and took a sip from his cup then focused his attention on Cas. “I’m gonna finish this beer, all right? Then you’re all _mine_.”

“It’s about time,” the man leaned in and sucked a kiss on his neck. “You’ve been driving me crazy-”

“Guys! I’m still _right the fuck here_!”

“Dean! Cas, I’m _so_ sorry!” Sam’s voice came out of nowhere, and all of a sudden he and Gabe were right in front of him, boxing out the rest of the wedding so they could talk somewhat privately. “Even though you’re kind of a dick to rig the betting, I really didn’t mean to screw you over-” his words were rushed, “And, you know, thank you for talking to me instead of collecting your half. It really means a lot. So, don’t worry. We took care of it.”

“Wait-” Dean raised a hand abruptly, “What do you mean, you took care of it?”

“It wasn’t a problem,” Gabe shrugged, “I had a lot of spending cash for this trip and haven’t used any of it, so really-”

“No, Cas already paid her the two hundred-”

“What?!” Sam balked, “We paid her two hundred, too!”

“Dudes!” Charlie started laughing, and when she did, she couldn’t stop, “You sooo got played! Jess only bet fifty bucks!”

The four men looked between each other, different levels of shocked. The sounds of Charlie’s cackling, was the background music as their expressions morphed from appalled, offended, to finally… fucking _impressed_.

They all turned away from the bar and scanned the room.

Sure enough, at one of the tables, Jessica had her eyes on them. Her legs were primly crossed, posture picture perfect, and she offered a sweet little wave and a wink.

“No. Fucking. Way.”

“I _knew_ she was a sly little thing…” Gabriel mumbled under his breath as he forced a smile, still staring at her.

“Whatever. She earned it,” Sam groaned as his palms covered his face.

“You guys are just thinking with the wrong head,” Charlie’s laughter finally died down, “Well, now that you’ve been _thoroughly_ humiliated, what’s the point of staying, right?”

Which Dean had to admit, was a _damn_ good point.

“Dibs on the hotel,” Gabriel immediately snapped, wiggling his eyebrows.

“No problem at all,” the older Winchester wrapped his arm around Cas’ waist, before lowering his voice and saying to the man, “Been dreaming about getting you into my bed for a while now.”

“Hope you’ve got a nice headboard for me to tie you up to,” his hand captured Dean’s face and kissed him hard.

“Guys! Just _leave_ already, you’re being gross!” Charlie groaned and ordered herself another drink.

“You just want the cash,” Dean broke away from the kiss, and rightfully accused her.

“Well, duh. But you just want the _ass_ , so it goes both ways.”

Dean jumped a mile high when his rear was very publicly groped, and had to admit it lit a fire inside him all over again. All the stress was forgotten because, _finally_ , he could _have it_. He could have _Cas_ , he could have him in his room, and he could have him all night, starting right the fuck now.

Hallelujah!

“C’mon, babe, let’s call a cab.”

The smirk that broke across Castiel’s face was nothing short of wicked. “I’ve already entered the number in my phone.”

The shiver that raked through Dean’s bones was violent. Cas looked like a predator. And he was happy to be eaten alive. All right, that was a little dramatic, must have been the booze talking, but it didn’t make it any less true…

“Can we split a cab?”

Sam’s voice snapped him out of his daydream about Cas stalking and tackling him like a leaping gazelle in the African wild, and dumped on him like a bucket of ice water. He glared over at his brother for being a potential cock-block, but that’s when he realized he wanted to get out just as badly as Dean did. Soooo fine. He couldn’t exactly refuse him.

Cas was already on the phone with the cab company and Dean swatted at his date, “There's gonna be two stops.”

Sam lit up like a fucking Christmas tree, and Dean also caught Gabriel with a dopey grin on his face. All right, so the two of them were pretty cute together. Although, he was kind of judging that they had _just_ had a quickie in a closet. They were now _rivals_ for pent-up sexual tension crown, and Dean wasn’t going to hand it over that easily. So, he was gonna make sure Cas and himself were dropped off _first_. That was his rule for sharing this damn cab ride.

“They’ll be here in ten. Let’s say our goodbyes.”

“One more shot for the road?”

Charlie snorted, “Naturally. Since you guys were love-at-first-black-out, it’s a tradition, huh?”

Dean found himself involuntarily twitching at the word ‘love.’ But then… he let it roll around in his brain… because… _huh_. Maybe… just _maybe_ that could be what this was. Not that he was gonna admit that anytime soon. But catching Cas’ smile (not his evil shit-eating grin this time) while he handed him a shot glass, gave him the warm-and-fuzzies, not _just_ the my-dick-is-hard vibes. They’d talk things out later.

Because, first and foremost, his dick needed appeasing. And Cas was really, really good at that.


	9. Chapter 9

They really should have expected it.

As soon as Dean walked up to Jo and told her they were leaving, she told him to wait, pranced across the dance floor, riiiight up to the DJ and stole the microphone. She killed the music, cleared her throat, and announced to the _entire fucking wedding_ over the speakers, “Ladies and gentleman! May I haaaave your attention!”

When Dean whipped his head around, he saw Cas looking _bored_ , while Dean, himself, felt like the bottom fell out of his stomach. Really?! How could he look so calm in the face of-

“Dean Winchester has lost the battle to the fire in his lions!” Her voice echoed through the room and was followed up by a roaring applause.

He couldn’t take it anymore, he buried his face in his hands, and did his damnedest to go to his happy place. Which was _not_ here. But… it helped, that he soon found Cas’ arm wrapped around him and patting him on his back.

Jo continued her tirade of humiliation.

“Good work, Mr. Krushnic! Novak? Whatevs. Now! May the victor - no, not _you_ \- Mr. Henricksen - this name shit is getting hella confusing - _please_ announce yourself and we shall play your victory song!” She swept her arm over the dance floor, and soon Charlie emerged from the crowd, straight-up fucking _moon walking_ her way to the DJ stand.

“Congratulations, Miss Bradbury! This one’s for you!” She slammed her hand down on the turntables and suddenly the lights dimmed, began flashing anew, and the sounds of Lady Gaga’s “Applause,” pulsed through the banquet room.

Dean wished he could dig himself deep enough inside Cas that he could fucking _disappear_ , but suddenly, he was yanked from his one and only form of solace, by fucking _Gabriel_  and lead back out onto the dance floor with the statement, “We have five minutes before the cab’s here, let’s dance to the sounds of your failure!”

And, why the hell not, he _did_.

\----------

He couldn’t make out or grope Cas this cab ride back, because Gabe was squished next to him and Sam was basically curled in on himself in the tiny front seat of a fucking _smart car_. Leave it to Cas to request a _box_ of a taxi. And it sucked, they were all crammed in here. But... at least it prevented any kind of public-indecency arrests, _right_? Last thing he needed was to end up in jail after that whole, ridiculous, hot mess they’d gone fumbled through that day. It didn’t keep him from staring hungrily at his date, though. Dean kept having to lick his lips because of the goddamn amount of _drool_ his mouth decided to secrete.

So attractive.

What _also_ sucked, was logistically, it made more sense to let Gabe and Sam off first. Hench, why his brother was riding shotgun. Cas had talked him down from a rampage, telling him to chill the hell out, and it had miraculously worked. Because Cas seemed to be a friggen wizard, or something, and had Dean whipped in record time. So. That’s why he was drooling instead. And waiting.

They pulled into the hotel, Gabriel and Sam jumped out with speeds so inhuman, Dean barely managed to shout out, “Use protection!” before they had disappeared into the lobby.

Then they were _finally_ alone.

Neither moved to spread out in the space, no ma’am, they were _quite_ comfortable jammed right up against one another, snug as a bug. They planned to stay just like this for the entire night, if possible. Dean was expecting Cas to say something that gave him an insta-boner, but instead… the words that came out of his mouth caught him off guard.

“Thank you for inviting me tonight, Dean. I had fun.”

There was an honest, sweet sincerity in those words that threw him for a loop.

“No problem. I, uh, was surprised you came. And really, really glad you did,” he squeezed his hand as he spoke. “Stoked you didn’t write me off as a psycho, because I know I probably would have.”

Castiel quirked a grin, “Your psychosis intrigues me.”

“Gotta thing for maniacs?” He teased and leaned in to nudge the man’s ear with his nose, “I gotta thing for _you_.”

He saw Cas shiver, and damn, if he wasn’t pleased with himself.

“You’re going to make it hard for me to head back to California tomorrow.”

And _that’s_ when Dean remembered _everything_. And all his motherfucking insecurities came to a head like a friggen battering-ram breaking into his brain. It was the same damn thing as a cold shower. He’d been able to pretend the entire night, hell, the entire time he’d been with Cas - that everything was fine and dandy, but it really wasn’t. He was actually falling for this dude, but _this dude_ was secretive as shit - this was  _seriously_  one of the _only_ times he’d offered up information about himself willingly and it was (probably) only because he was drunk. And that was fucked up. And drunk Dean couldn’t exactly ignore it.

“You never told me you were from California.”

The silence in the cab was uncomfortable.

When Cas spoke again, his words were selective and brief. “Oh? I thought I had.”

“No, Cas. You’ve literally not told me a thing about you. Even when I _ask_.” He could feel his own body go rigid. “What’s up with that? I mean, uh, I’m not a stalker, or anything, but the only shit I know about you, I had to find out from _Charlie_. And it’s not like I haven’t been tryin’ - you’re just blowing me off. You’ve been doing that from day one. I want to get to know you but… you don’t seem like you _want_ me to.”

Castiel pursed his lips together and wouldn’t look at Dean. And, of fucking course, that was when the taxi arrived right outside Dean’s place. He grunted as he pulled out his wallet - not allowing Cas to pay for the ride, since he paid off Jessica - and handed the cabbie the fare. They both got out and walked the distance from the road to Dean’s in silence. Shit. This was not how he’d wanted this to go.

Once inside, he threw his jacket haphazardly over the couch, and was quickly knocked into the wall. Cas was on him in no time, his mouth hot, and Dean knew he was trying to shut down any more conversation. But it wasn’t gonna work. Yeah, Dean usually melted under his touch, and he was beginning to, which was why he had to push him away before he’d reached the point of no return.

But, shit, Cas was strong.

Dean’s _frustration_ was _stronger_.

He wrenched out of his grip and stalked off to the kitchen to grab two beers. He had to get himself (AKA the tent in his fucking pants) under control. When he stomped back out, Cas was still in the entry way, looking at the vinyl flooring. Dean shoved the cold glass bottle into his hand and took a seat on the couch - snapping his fingers to get Cas’ attention and to follow his lead. He did so - but quite grumpily.

“I thought we left early so I could fuck you into next week.”

“Don’t you dare,” Dean pointed a finger. “If we don’t talk about this now, we’re _never_ gonna. And it’s something that’s been bothering me for a long fucking time, all right?”

Cas’ long fingers were peeling the label from the bottle, after he’d taken his first sip. “It’s not like I don’t want you to know about my life.”

“Could’ve fooled me.”

“I don’t know… the protocol.”

“Protocol?” Dean repeated back, with a raised eyebrow. “The _hell_ are you talking about?”

Cas guffawed and slumped backwards on the couch, taking a nice, long chug of the beer. “Were we a one night stand? Are we supposed to keep it that way? Is it casual? I’m unsure, because I’ve never had one.”

“Wait.” Everything in Dean’s mind finally pieced together. “You’ve never taken someone home from a bar? Like, _ever_?”

“No.” His annoyance was magnified. “I’ve only ever been in relationships - this is completely new, and I have no idea how to handle it. I was led to believe that casual sex is completely different from a relationship, that it’s all about intercourse - and if I let my guard down and you find a way into my life… I won’t know what to do. You _have_ , so I feel like I’ve messed up already. I’m out of my depth.”

“Huh.”

“Huh?” Cas echoed, chugged the rest of the beer, and then slammed down the empty bottle. “Thank you _so much,_ for your eloquence.”

“No, no, no.” Dean waved his hands in front of him, hoping for a take-back. “I mean, I get it, that all makes sense. But you don’t give your number and chat regularly with people you’re having ‘casual sex’ with. Hell, when we were fucking drunk texting, we decided on _goddamn sunflowers_ for our _wedding_. I’d say it’s obvious I want a little more, right?”

“Dean. You’re always drunk. I don’t know what I can or can’t take seriously when it comes to you.”

“Hey! That’s not true!” He defended quickly. “It’s just celebration season, dude! I can’t be held responsible for my actions! Besides, when I invited you, I was completely 110% sober. So there’s that.”

Castiel crossed his legs and looked at him. It was a good, long look before he tilted his head and asked, “So… what do you want out of this?”

“Cas… I like you. Like… falling in like with you-”

“That’s a thing?”

“Shut up. I wanna be with you. And I’m sorry I didn’t clarify earlier, but I didn’t know that you had questions. If I had known, I would’ve freakin’ shouted it from the rooftops the second you were confused.” He leaned in and took the man’s hand. “I mean, if that’s all right with you.”

“Yes,” he nodded and chuckled, “I think I’ve fallen in like with you, too.”

“That’s great news!” Dean set his beer down on the table, and launched himself across the couch until he was pinning Cas down. “Now, where were we?”

The dazzling grin on the man’s face took Dean’s breath away, as he looked up to him with so much fucking affection. It was dizzying. He almost didn’t want to kiss him - he almost just wanted to get lost in his eyes… but that wasn’t happening. He’d been waiting _all_ fucking _night_ for this, so the moment their lips met - it opened the flood gates.

Dean let his body weight sink down on Cas, as the man’s arms instantaneously wrapped around him, pulling him closer. They didn’t want anything separating them, and the clothes were chafing, so those needed to go, like, _yesterday_. But he couldn’t bring himself to pull away from the mind-blowing kisses. Cas’ tongue was pure magic, running along his teeth, coaxing his lips into his mouth so he could suck them swollen and tease little whimpering noises from his chest he didn’t even know he could make.

Their hips quickly found the perfect rolling motion - rocking in sync - while their hands wandered and tugged at the grating fabric still between them. They didn’t want to pull away, but they had to. And Dean had another suggestion, once his mouth was free to form words, even if they weren’t perfect sentences, “Bedroom. Now.”

He hopped off Cas and multitasked - unbuttoning his shirt (because he’d _rented_ his suit, _dammit_ , and couldn’t afford Cas ripping this one apart, too) and swaying in his steps on the way to his room. He peeled off his shirt and quickly stripped himself of the undershirt, belt, trousers, socks, and underwear ( _Jesus, why were there so many layers?!_ ) and plopped his _very_ naked ass in the middle of his bed.

Cas had been enjoying the show, and only managed to unbutton his shirt and remove his belt by the time his partner was full-frontal. He was gaping at him with thirst, his hands conflicted as to whether he should be stripping the rest of his clothing or worshiping Dean bare skin. It was making him _insane_ , as he watched the man spread out proudly on the bed, cock throbbing and hard between his legs and just _begging_ for touch…

He only managed to rip off his shirt and pants before he attacked.

And _what_ an attack it was.

Castiel didn’t need a fucking tie, he expertly grabbed both of Dean’s wrist with one of his hands and immobilized them above his head with a border-line violent force. Where did he get all this muscle? It was quickly climbing the list of Dean’s favorite kinks, and he could feel the pre-cum oozing from his dick, while Cas jerked him around and positioned him _right_ where he wanted him. His mouth was just as frenzied, nipping at his neck and collarbones - he was possessive. Now that they’d come clean about their feelings, Cas was a mad man, needing to _claim_ , needing to _mark_ Dean as his own.

Each and every bite and hickey made Dean’s hips arch into the air, the frantic and primal _want_ shocking him like lightening. He moaned when Cas reached his hipbones and the man used his free hand to hold him down in place. Dean couldn’t rock forward anymore, he was completely at Cas’ mercy when he ruthlessly kissed the sensitive skin of Dean’s fleshy hips and inner thighs.

He released his grip on Dean’s wrist and whispered (his breath ghosting against Dean’s cock), “Can you keep your arms there, or should I tie you up?”

“We’ll see…” it was honest. He could _try_ to keep his hands to himself, right?

Cas quirked a smile, “Good.”

He shifted his body down, until he was between Dean’s legs and spread them obscenely wide. This time, they weren’t fucking with the lights on, but the street lights cascading into the room still cast enough light for him to feel _vulnerable_. But in a good way. He _trusted_ Cas, and he was turned on beyond belief.

Castiel manhandled his pelvis enough to slip one knee under him, and, _all right,_ Dean _hoped_ he knew where this was going. He watched Cas duck his head and let his mouth skip right over his neglected cock to lavish one of his balls and suck it into his mouth. Dean hissed at the incredible pressure and would've bucked if he wasn’t held in place. His mouth dropped open as Cas’ tongue worked further down and, _fuck_ yes, lapped over his hole.

With one hand holding down his hips, and the other gripping the globe of his ass, he stretched his cheek open and tongued Dean’s completely exposed opening. The moaning reached new levels as the wet-hot intruder dove inside him and started pumping in and out. Dean wriggled his hips, trying to get _more_ , but apparently, that wasn’t what _Cas_ wanted.

Because he was answered with a loud, firm _smack_ on his ass.

Dean yelped and stopped moving all together, but the sting of Cas’ hand… felt _really fucking_ good. Was that weird? Was he turning into a freak?

“You’re misbehaving,” Cas’ voice vibrated against his hole, and the heat of his breath against the wetness made him tremble.

He knew he wouldn’t be able to form coherent words, so he didn’t even try. The next best thing he could even come up with was a whine. He didn’t know what he was even _trying_ to convey. Sorry? I’ll be good? Fuck _no_ , I won’t be good, please spank me again? _What was life_ … he was gonna _explode_ from arousal at this point, goddammit, Cas.

After flattening his tongue, Cas dragged it from the cleft of his ass, dipping into his puckered entrance, over his balls, and finally, _finally_ all along the entire length of his cock. He stopped at the tip and greedily sucked off at the precum beading at the head. “If I didn’t know better, I’d say you enjoy being bad.”

And, all right, Dean could at least nod enthusiastically to respond to _that one._

Cas looked impossibly more turned-on, if that were possible, “We’ll save that for another time. I’d very much enjoy spanking your rear until it’s _numb_ , but now… I can’t go much longer without being inside you.”

Dean could get down with that. He nodded vigorously again, and reached out his hand to the nightstand, before Cas could even ask. Dean pulled out the lube he’d bought especially for this weekend, and a condom and tossed it (exceptionally ungracefully) at Cas. “Been waiting for this too, babe.”

“Turn around.”

He scrambled to follow the order (but not before sneaking a peek as Cas removed the rest of his clothing) because _damn_ was his authoritative voice jizz-in-your-pants worthy. Dean could never get enough of this man… maybe ‘falling-in-like’ was an understatement. Cas drove him wild in every way possible, in ways he didn’t even see coming. Every second with the man was-

Dean grunted and threw back his head when Cas plunged in the first finger, right up to the knuckle. It caught him off guard - dammit, he needed to _focus_. Cas slowly worked it in, more gently than he had to, considering - just this morning - he’d had already shoved a finger in his ass during their shower. The second one wasn’t as smooth, but Cas knew what he was doing, and twisted his digits in _just_ the right way to easily slide them deep inside. He wasted no time finding Dean’s prostate and filling him with that firework-pulse, a promise of what was to come (hah, Dean was proud of that pun). It made him relax more quickly, eager to get things going - an incentive. The third finger was kind of rough, and Cas knew it, so at the same time he was slowly soothing it in, he reached around with an already-lube-slicked hand, and stroked Dean’s weeping cock.

Cas kissed his back, open mouthed and tenderly as he started pumping the fingers in and out of his ass, gaining a rhythm in time with his fist. He _really_ needed him to relax - he wouldn’t feel right fucking him until he prepped him with a fourth finger. And, yeah, Dean knew this, too. The way Cas was touching him felt so fucking good, but his ass was born-again-virgin tight, since he hadn’t hooked up with anyone since Cas.

How was _that_  for really digging someone?

Except, it kind sucked right now.

It would all be worth it in the end, he knew, and as he felt the tip of a fourth finger push against his hole, he had to tell himself over and over _relaxrelaxrelax_. Castiel’s sweet kisses were helping. Shit, he’d never felt so _treasured_ during sex. It was a really bizarre, but not unwelcome, feeling.

When he really started to analyze that, was when he realized he was stretched full, and Cas was whispering in his ear, “You ready for me to fuck you, baby?”

“Hell yeah,” he wiggled his hips, and arched back into his fingers once, before they were pulled out.

He heard the tearing of the foil, the squirt of the lube, and before he knew what he was saying he suddenly asked, “Uhh, can you fuck me on my back?”

Since, apparently, these days they were communicating with _actions_ more than _words_ , Dean found himself shoved onto the mattress, air knocked from his lungs, face to face with adoring blue eyes. He was smiling, too. And, ugh, that freakin’ _smile_ …

“I don’t want to fuck you on your back,” Cas suddenly stated, and Dean turned pale.

Had he said something _wrong_? Was this the part when Cas took off? He didn’t think this was a _bad_ thing - this was the way they’d done it before, so why wouldn’t Cas wanna? Dean was so confused, frazzled, and thinking the worst possible scenario. Castiel noticed that immediately, and quickly stopped all the destructive thoughts and devastating conclusions running through his head.

He dove his head forward and kissed him soundly. While their lips were pressed together, tongues stroking and praising one another, Cas positioned the head of his cock against Dean’s entrance. Which confused him even _more_.

“Cas-” Dean cried out as his body became overwhelmed by the sheer size of Cas - starting to push in.

“I told you, Dean,” he waited for the man to relax before inching forward, at a maddeningly slow pace, “I won’t _fuck_ you on your back.” Finally, when he bottomed up, Dean’s arms flew around him, and he finally looked at the man, Cas finished with, “But I _will_ _make love_ to you on your back.”

Dean’s cheeks flushed crimson, and he was trying to tell himself it was because of the huge dick currently balls deep up his ass. But, _nope_ , he couldn’t lie to himself. Fuck, fuck, he couldn’t get emotional _now_ , but looking at how fucking _authentic_ Cas was? His heart was doing weird things.

So he gulped and responded, “That’s okay, too…”

With a light laugh, Cas slowly pulled out to see Dean’s reaction - which was _thoroughly_ ecstatic. He thrust back in and kept his watch, half to make sure he was all right but mostly (at this point) to watch him come undone. And he was coming undone by the _second_. His face was wrecked in ecstasy, mouth shaped around the rasping word, “more,” and his neck exposed, and ripe for the taking.

So Castiel took.

He pulled out enough each time to snap his hips forward with enough force to rock his lovers world. Dean’s legs wrapped around Cas’ hips, urging him back, and attempting to force him deeper inside. He was getting lost, and he loved every second. Cas’ hand reclaimed its grip on Dean’s cock and started pumping him all over again. Between his skilled hand, his friggen mouth-magic-sorcery on his neck and, _oh yeah_ \- there he was again - hitting that sweet spot, Dean was done.

“Just like that… just, yeah, Cas,” his words were shadows of syllables lost in the panting coming from his chest. “L-love-”

Then he was cumming, ropes of white spurting from his cock, covering both their bodies as he shouted Cas’ name. He didn’t slow his pace, even for a second, pounding savagely into Dean. If anything, he hurried it up, because if he had heard him right, there was the _first part_ of the ‘L’ word, being uttered through the waves of his orgasm. And, fuck, _that_ was the thing that sent Castiel spiraling over the edge.

He muffled his own cries in the crook of Dean’s neck, his arms reaching out to wrap themselves around Dean while he came. He didn’t care that cum and sweat were lubricating their bodies as he rode it out. He found it ridiculously sexy, and when he pulled away, the kiss that Dean stole ripped out any remaining breath from his lungs.

Cas didn’t want to move from where he was draped, he loved the angle, the front row seat to watch Dean purr with pleasure and contentment. Every now and then, as they came down from the high, Dean would steal a kiss from Castiel’s lax lips and hum into the feather soft touch. It was addicting.

When he finally spoke, again, Dean’s voice was full of mirth, “I will literally _fillet you_ if you even _think_ about running out on me this time.”

With a laugh, Cas peeled himself off and responded, “The only place I’m off to, is to get a washcloth to clean up,” he brushed his lips over Dean’s forehead, “Is that acceptable?”

“Yer pushin’ it, buddy.”

“I’ll be right back.”

Dean happily watched Cas’ naked backside stroll off to the bathroom and couldn’t help but think how good he looked here. He completed the place - it was like he _belonged_. Like he’d been here all along… When he reappeared, and took special care cleaning Dean up with the warm cloth, Dean word-vomited:

“Can I keep you?”

Cas didn’t respond until he’d wiped Dean down completely, and then said, “I think I’d like that.”

“Yeah?”

“On one condition,” he lifted up the sheets, and tucked them both in, “You don’t snore. And you don’t hog the covers. And you don’t whine about being the little spoon.”

“That’s an awful lot of stipulations, Cas,” he shifted around, so they were face to face, and brushed their noses against one another. “You’re kinda high maintenance, aren’t ya?”

“I seem to recall, in the throes of passion, you may _love it_ ,” he sucked Dean’s lower lip into his mouth and tugged.

“Uh… about that,” he blushed, and stammered for the words. Until he realized, “You know what? About _nothing_. I _meant_ it. So, there.”

“Your intelligence never ceases to amaze me, Winchester.” Cas started to laugh, wrapped his arms around Dean and drew him even closer. “So how about actually getting to cuddle, for the first time ever?”

Dean’s jaw dropped in faux-shock. “My heart be still, this is the best day of my life.”

“If this is the best day of your life, just you wait,” Cas grabbed him and pulled him to his chest, until Dean’s body completely relaxed, their breathing linked up, and their chests rose and fell in time. “I’ll outdo myself night after night to give you even better days to look forward to.”

“Shit, Cas,” not even a fuckin’ bulldozer could wipe the grin off his face, “I think you just put Benny and Jo’s vows to shame.”

“You should see what I can do with some time alone, a pen and paper.”

“Is that a threat?” Dean peered up and wiggled his eyebrows.

Cas leaned down, and sealed it with a kiss - “It’s a promise.”

**Notes for the Chapter:**

> Woah. This story FLEW BY! All that's left is the epilogue. Hope you've enjoyed the ride <3


	10. Chapter 10

**Notes for the Chapter:**

> Here's the epilogue!

When Dean woke up, it was to the very naked back of Castiel Krushnic: former Russian douchebag prowling a piano bar in Chicago transformed into what _could_ be the love of his life ( _it's too early -_ Dean told his brain - _stop that!_ ). The man was up, and leaning on his side, typing away on his phone. While Dean was confused, and didn’t particularly like this, he _did_ like that it gave him a spectacular view of his ass _and_ he could still see the red marks left over from his nails raking along Cas’ shoulder blades. Oops, it looked like he’d gone a couple rounds with a tiger. Dean regretted _nothing_. He immediately noticed that his hand was still slung low around Cas’ hips, even if the man was leaning away from him.

“Well, shit, looks like you let me be big spoon last night, is that a deal-breaker?” Dean cleared his throat and decided he didn’t give a flying fuck _what_ Cas was doing, he yanked him back because he was cold, dammit.

“Dean!” Cas barked, shooting him a glare and rearranging his phone as it _continued_ to capture his undivided focus. “You’re going to make me click the wrong link and I’ll end up flying to Timbuktu. I don’t even know what the native tongue _is_.”

“I’ll show you _my_ native tongue,” Dean teased and pressed a sloppy kiss on his shoulder to emphasize his point. “Waitaminute. Why are you flying?”

“I’m changing my flight,” he stated casually, like it was the most obvious thing in the world.

“Changing your flight?” Dean repeated, his mouth a little dry and he _hoped to God_ Cas was saying what he _thought_  he was saying.

Because if he wasn’t, and he got a new fucking case somewhere else and was changing it for _that_ reason, he was going to kick his ass _so_ hard for getting his fucking hopes up.

“How long would it be appropriate for me to stay for a visit?”

“Shut the fuck up,” Dean couldn’t keep the grin off his face. Best. News. Ever. “Forever. Duh. You don’t even have to book a flight back, put that away, dummy.”

Cas’ laugh was hoarse, as he balanced his phone in one hand and reached the other downward to run his fingers through Dean’s hair. “You’d get tired of me. We have to keep _some_ of the mystery alive. At least for a little while.”

“Mm, too mysterious. How will I know if I even like you if I don’t get to know you?” Dean began to roll on top of Cas before he was forcefully shoved away.

“Really, I’ll end up in fucking India. Give me a date, Winchester.”

“It’s Sunday? Stay through this weekend. I can take some time off, since I have friggen vacation days saved up the wazoo, and half my team was at the wedding to see our dumbasses together, so you know they've gotta cut me some slack.” Dean allowed himself to be pushed and collapsed back on the bed, but that didn’t stop him from pulling Castiel tighter. “How does that sound?”

Cas bit his lip and glanced over at Dean - he looked a little ashamed.

He clicked through his phone - Dean eavesdropped - and saw that Cas, indeed, decided to take his advice. Once the flight was booked, he set it down and spoke carefully, “I’m rather embarrassed. I don’t even know what you do for work, Dean.”

“Hah.” Dean snorted, right against Cas’ neck and effectively made a weird raspberry-skin-vibrating sound that the other man smacked him in the head for. “See? We need to dispel some of the mystery. And now we actually have time to do that.”

“Are you going to tell me, or not?” He grumbled, rubbing his neck because now there was drool on it, and it felt weird. But for as much as Dean’s teasing made him fussy, the man’s actions were adorable, and he nuzzled him.

“I’m a cop, dumbass.” Dean pressed a kiss against the stubble of Castiel’s cheek. “Benny’s my partner, and half the groomsmen work at the station with us.”

“Hmm,” Castiel mused aloud, before glancing at Dean with hungry eyes.

Dean gulped.

He _knew_ that look. Cas had gone from zero to _I’m-going-to-eat-you-alive-and-fuck-you-into-next-week_ in two seconds flat. That _had_ to be a new world record, or something. He was in deep shit.

Next thing he knew, he was flat on his back with Cas leaning down and sucking his neck.

“You mean to tell me-” he nipped his collarbone, and -oh yeah- _that_ was gonna bruise, “- we were teasing about ties all day yesterday-” he rolled his hips against Dean, his hard cock rutting against his thigh, “-when you have _fucking handcuffs?!_ ”

Even if the breath was stolen from his lungs, Dean was still able to snort a sarcastic, “Damn, Cas, if _this_ was all it took to get your engine revved up, I woulda brought ‘em out on the first date-”

Castiel didn’t want to hear anymore - he proceeded to _eat-him-alive-and-fuck-him-into-next-week_ with vigor and eagerness.

\-------------

While everyone in the Harvelle-Lafitte wedding had made arrangement with the station to miss work on Sunday, when Monday morning came around, it was a _whole other story_.

The new sergeant of the prescient, Naomi, who had just _recently_ transferred over - was _swamped_ with calls. Little did she know what she was getting herself into, when she agreed to take the job.

At least Dean Winchester, who did, indeed, have a surplus of vacation days, had the decency to call in _Sunday_ and let her know he wasn’t going to be in for the rest of the week. That wasn’t a huge deal to begin with, since his partner, Benny, was already out on his honeymoon - so all Dean would be doing that week was desk work, anyway.

No, the _real_ problems came _Monday morning_.

Gadreel had, apparently, managed to break his leg at the after-party (what kind of a wedding had an after-party, for God’s sake?!) while playing a strange hybrid game of hide-and-seek and karaoke (he didn’t explain it very well, being high on pain medication) and was still in the hospital, waiting to get pins put in his fibula. Of all the idiotic things…

… it didn’t even begin to compare to the call she received from Samandriel.

Well, the call wasn’t even _from_ Samandriel, at first.

It started off with the question, “Will you accept a collect call from the Wayne County Jail?”

“Excuse me?”

“It’s a yes or no question, ma’am.”

She was surprised, thinking this must be some kind of _joke_ or prank call, but accept, none the less.

“Hi… uh… I’m mortified now, because I didn’t think they were going to ask you to accept the call and I was just gonna call in sick so hah-hah, I guess I’ll call-in-jail instead?” Samandriel’s voice was choppy and, yes, full of shame. “I don’t know how long I’ll be here… I’m not exactly sure where I am, even…”

Someone in the background shouted, “Detroit!”

“Oh, thanks!” He turned his attention back to Naomi, “I guess I’m in Detroit.”

“What are you doing in Detroit?” Her voice was even, and she was trying to keep from flipping her shit.

“After the wedding-”

“Why am I not surprised, this has to do with the wedding!” Her rage was bubbling up by the second. “Sorry, please continue.”

“Yeah, uh, well… have you seen The Hangover? It's kinda like that. I’m still trying to figure out what happened… I’m really confused right now.”

“Why the hell didn’t you go to Vegas? Why _Detroit_?”

“I didn’t even _know_ we were _in_ Detroit. All I know is our friend Hannah really likes Eminem and Jessica was on the prowl for some ‘dark chocolate.’ Women are terrifying, I’m never doing anything like this again but they just kept making me drink _tequila_ and then I swear to god there was _moonshine_  which I didn't even know was legal and before I knew it-” his voice was getting higher and more hysterical by the moment.

“ _Breathe_ , Samandriel,” Naomi commanded. “I’ll make some calls. God, Lafitte is gonna get his neck ringed when he gets back.“ She paused for a moment, gathering herself, “Just wondering, why didn’t you use your one phone call to get bail from a friend? Or maybe contact a damn  _lawyer_?”

“Well…” his laugh was an awkward, quiet titter, “Honestly, I’d rather be stuck in _here_ than face _your_ wrath…”

“Interesting. Very smart choice.”

\--------------

Jessica stirred awake, and by the fancy lights on the ceiling knew she in a hotel room.

She thought she remember a casino?

Was she in Greek Town? At the MGM?

She couldn’t remember a damn thing…

All she knew is she turned her 200 bucks into a couple grand, and that was fine by her. _Fuck yeah_ , Detroit was a _fantastic_ choice.

Even though her head was throbbing and she couldn’t remember much outside the rounds of (was it Hennessy?) shots after her big celebration and dancing through the streets - it had to have been a good night, right? She was pretty sure she gave out ridiculous amounts of money to some random bums... who were probably high off their asses right now… but she couldn’t worry about that, because there was a _very_ good chance she was going to throw up.

She jerked to sit up and _groaned_ \- not caring if she woke anyone.

She was in a massive fucking California king, rotating bed and was tucked in against Meg, Ruby, Hannah and two strangers. And they were all _naked_.

She rolled her eyes, and mourned the life choices she was making as of late, “Not _again_.”

\------------

“Come with me to Chicago. I gotta get back for work, but I wanna steal you away,” Gabriel admitted as he tugged Sam to the edge of he bed and cupped the sides of his face. “Didn’t have a reason to stay... so I gotta leave today. But I wanna kidnap you, kiddo.”

Sam leaned into the feeling of his warm palms for a second and let himself get caught in Gabe’s pleading eyes. The man _meant it_. And Sam had come to realize there wasn’t a lot he was serious about - this was _something_.

He laughed and shrugged, “I don’t know. I don’t exactly have the money for a plane ticket right now, and-”

The man’s hand slapped over his mouth - it wasn’t a finger to his lips like _most people_ would have used to silence a lover.

But Gabe _wasn’t_ most people.

So, he had no problem at all, basically gagging his new boyfriend.

Romantic.

“Nuh-uh-uh. I got money. You can be my sexy trophy boyfriend and warm my bed alllll day until I’m at home,” he winked, “Just kidding, of course. But not about the plane ticket. And I’ve got a nice loft in Chicago and there’s plenty to do around the city and I work late, anyway. I just… don’t wanna leave you, yet. Besides… I heard from Jess that she got the scoop from Dean you’re in the process of ‘finding yourself.’ Why don’t you try to find yourself in Chi-town?”

Sam’s voice was muffled behind Gabe’s hand when he didn’t remove it right away. When he did, he didn’t let Sam speak for a second, and decided to kiss him again, because why the hell not?

When he pulled away, Sam kept his eyes shut just a second longer.

He swallowed, and when his eyes finally fluttered open he asked, “Finding myself, huh? _That’s_ what Dean thinks of me?”

“Not a bad thing, Moose. I’d be glad to lend some assistance,” even though he wiggled his eyebrows and never stopped being a cheeky asshole, his gaze never left Sam.

“Sure ya would, old man.” He chuckled out, which earned him a light punch in the shoulder.

“Respect your elders. You’re avoiding me.”

“No-” Sam said quickly. “Just… thinking, is all.”

“Think fast,” he pecked Sam’s lips quick before finishing his statement with, “I’m gonna go jump in the shower.”

Gabriel left without another word, because if he was being honest… his stomach was tied in goddamn _knots_. He couldn’t do much else, outside of _begging_ , to bring Sam back with him… but that just wasn’t something he did. It wasn’t his style… and if he had to beg in the first place, was that even the kind of relationship he _wanted_? Nah, he wanted the kind where they fell madly in love, and it broke all boundaries and overcame all hurdles standing in its way because-

\- no, not really.

He just really, really liked Sam and thought there were bigger and better things out there for the kid than Lawrence freakin’ Kansas. He didn’t have anything against the town, don’t get him wrong, he just saw things… _different_ for Sam. In the time - so far - that he’d gotten to know him, he didn’t fit in here, and who knows if he fit in with Gabriel, but he'd kick himself if they didn’t even try...

Gabe sure as hell wanted to try.

He groaned as he tugged off his clothes with more force than necessary and hopped into the shower. At least it had good water pressure to distract him for a hot second, right? No, nothing was going to distract him, if he was honest. But… that didn’t mean he wasn’t going to take his sweet time in here, putting off what _could_ be rejection because that would hurt a whole hell of a lot, and he’d inevitably end up with the flying companion of many a Bloody Mary if it wasn’t a Sasquatch.

And that trade just _sucked_.

His eyes were closed under the spray, and he was so damn caught up in his own mind he nearly _yelped_ when he felt arms wrap around him. He was no longer alone.

“Jesus!” He snapped, “Warn a dude!”

“Sorry,” Sam was fucking _giggling_ , “Next time I won’t join you.”

And, yep, to Gabe utter glee - Sam was, indeed, very _very_ naked.

“Scratch that. Do whatever you want, just let me ogle, all right?”

“Ogle away,” he head-butted the shorter man and stated, in a hushed voice, “Hope you’ve got a bigger shower in Chicago…”

“Oh yeah?” The grin that spread across Gabe’s face was nothing short of brilliant, as he grabbed a handful of Sam’s hair and yanked him down to his lips. “The shower’s _fantastic_ , although I may have to get a bigger _bed_ …”

\----------

Jo and Benny were curled up under an umbrella on the beach, sipping the most stereotypical drinks with little goddamn shish-kabobs of fruit in them... and laughing their asses off. Benny had one arm wrapped around his wife, as he peered over his sunglasses down at her phone, pleasantly buzzed and enjoying every second of it.

“Dude, we caused way more trouble than we thought, babe,” Jo beamed wickedly and playfully bit Benny’s neck before reading the latest text:

“This is from Jess - _Apparently there was a ménage a FML last night and I can’t find Samandriel, do you have his number?_ ”

Jo snorted, took a long chug of her drink, “I’m responding, ‘ _Did you lose him up your whore vagina?_ ’”

“Isn’t that a little mean, darlin’?”

“Hell no, you’re not a girl, this is _kind_.”

He shook his head, “I’ll never understand you ladies. I think my favorite so far - because it was our fault they got together - was Gabe texting you _‘If you’re ever hunting Big Foot (with a big dick), there’ll be sighting in Chicago wink face.’_ ”

“Ughh, baaaabe,” she made a very unladylike growl in the back of her throat, “You can’t just _say_ ‘wink face.’”

“Why not?!” He looked offended, wide-eyed and everything.

“Because!” Jo scrolled through her phone, and cackled as she read a new message. “This has to be the best one! It’s from Cas…”

Benny looked over his shoulder, back to the phone, and started laughing along with her.

_Joanna I apologize for interrupting your honeymoon I have a question for your husband_   
_Say you had a pair of handcuffs, locked them, and forgot the key at work…_   
_What would be the most useful tool to pick the lock? Is that possible?_

Benny stole the phone from Jo and typed:

_Hey Cas this is Benny_   
_Tell Dean to get comfortable_   
_And I’m gonna use this as blackmail for the rest of his life_

**Notes for the Chapter:**

> THE END!! Thank you so much for reading xoxo


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